US20050198742A1 - Chemical compounds and methods for removing dye - Google Patents

Chemical compounds and methods for removing dye Download PDF

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Publication number
US20050198742A1
US20050198742A1 US10/505,248 US50524804A US2005198742A1 US 20050198742 A1 US20050198742 A1 US 20050198742A1 US 50524804 A US50524804 A US 50524804A US 2005198742 A1 US2005198742 A1 US 2005198742A1
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United States
Prior art keywords
leveling
dye
polyester
mixture
composition
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US10/505,248
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Raymond Berard
Connie Hensler
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Interface Inc
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Interface Inc
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Priority to US10/505,248 priority Critical patent/US20050198742A1/en
Assigned to INTERFACE, INC. reassignment INTERFACE, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HENSLER, CONNIE D, BERARD, RAYMOND A
Publication of US20050198742A1 publication Critical patent/US20050198742A1/en
Abandoned legal-status Critical Current

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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13Fugitive dyeing or stripping dyes
    • D06P5/137Fugitive dyeing or stripping dyes with other compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29BPREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02Separating plastics from other materials
    • 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
    • C08J11/06Recovery or working-up of waste materials of polymers without chemical reactions
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42Ethers, e.g. polyglycol ethers of alcohols or phenols
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29BPREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02Separating plastics from other materials
    • B29B2017/0213Specific separating techniques
    • B29B2017/0293Dissolving the materials in gases or liquids
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING 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
    • B29K2067/00Use of polyesters or derivatives thereof, as moulding material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29LINDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00Other particular articles
    • B29L2031/731Filamentary material, i.e. comprised of a single element, e.g. filaments, strands, threads, fibres
    • 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
    • C08J2367/00Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613Polyethers without nitrogen
    • D06P1/6138Polymerisation products of glycols, e.g. Carbowax, Pluronics
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6498Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651Compounds without nitrogen
    • D06P1/65106Oxygen-containing compounds
    • D06P1/65118Compounds containing hydroxyl groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651Compounds without nitrogen
    • D06P1/65106Oxygen-containing compounds
    • D06P1/65131Compounds containing ether or acetal groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • 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

Definitions

  • This invention relates to chemical compounds and methods for removing dye from polyester fibers, and more particularly to removing dye from panel fabric made from recycled poly(ethylene terephthalate) fibers.
  • Panel fabric also known as vertical fabric, is used in furniture upholstery, wall systems and tackboards. Panel fabric is increasingly produced from synthetic materials such as polyester, most commonly PET (poly(ethylene terephthalate)). Panel fabric is replaced periodically and as a result, is often discarded in landfills. Many of the materials used in panel fabric are not biodegradable; thus disposal of it contributes to the environmental problems that arise from the over-use of landfills.
  • the PET in the panel fabric would be recycled into fiber that can be reused, e.g., suitable for weaving into new panel fabric. In this way, the material is not only rendered recyclable, but recyclable in a sustainable fashion, decreasing the need for virgin PET or PET recycled from bottles, which can then be put to other uses.
  • any PET that may be recovered when garnetted into loose fibers is unsuitable for significant reuse in panel fabric and carpet manufacturing.
  • the staple fiber is generally too short to be reused in the yarn spinning process at more than about 3%. If the fibers could be melted, pelletized and extruded into full-length fiber, they could be recycled at about 100%.
  • the presence of dyes in the fibers makes them difficult to melt and extrude. The dye molecules char and burn at extrusion temperatures, forming a residue that blocks the extrusion spinnerets. As a result, a process capable of removing dye before extrusion is needed.
  • the invention solves some or all of the above mentioned problems by providing methods and compositions for removing dye molecules from polyester, PET in particular.
  • the invention allows the PET to be reused by pelletizing and extruding it into fiber suitable for panel fabric or other applications calling for virgin PET, without disrupting the extrusion process by dye molecule charring.
  • the invention addresses the problem of downcycling the PET in panel fabric by providing a way to use recycled PET that is economically and environmentally of the same value as the panel fabric itself.
  • the PET can be melted, extruded and reused as panel fabric.
  • the invention is an improvement over existing processes because it completely removes the dye molecules from the PET, instead of breaking only the chromophore of the dye.
  • the PET may be melted and extruded, without remaining dye molecules burning or blocking the extrusion spinnerets.
  • the method of the present invention does not damage the PET by swelling.
  • a method for removing dye from polyester fiber or fabric by contacting the polyester with a dye removal composition containing an aqueous solution of at least one leveling agent; heating the mixture of polyester and dye removal composition until it reaches an elevated temperature and pressure level higher than the equilibrium pressure of the dye removal composition at the elevated temperature; cooling the mixture; and removing the decolorized polyester from the mixture.
  • a composition for removing dye from polyester includes an aqueous solution of about 0.5 wt % to about 8.0 wt % of at least one leveling agent.
  • the invention in another embodiment, relates to a device for removing dye from polyester according to the present invention.
  • the device includes a sealable vessel and a dye removal composition.
  • the dye removal composition includes an aqueous solution of about 0.5 wt % to about 8.0 wt % of at least one leveling agent.
  • the invention is also directed to a method for recycling panel fabric comprising polyester.
  • the method involves removing from the fabric any structural elements, removing the dye from the fabric using a dye removal composition comprising an aqueous solution of at least one leveling agent, recovering the polyester fibers, melting the fibers, pelletizing the melted fiber and extruding the pellets into full-length fiber.
  • the dye removal composition comprises at least one leveling agent selected from the group consisting of anionic leveling agents, nonionic leveling agents and mixtures thereof.
  • the dye removal composition further comprises at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers.
  • Leveling agents may perform one or more of these functions in addition to their function as leveling agents.
  • the invention provides for a method of removing dye molecules from polyester fiber, and is particularly useful with PET fiber.
  • the polyester may be used in the process as woven fabric or, alternatively, garnetted into loose fibers.
  • the polyester is contacted with a dye removal composition comprising an aqueous solution of at least one leveling agent. This may be conveniently done in a standard dyeing vessel commonly used for disperse dyeing of polyester, which is sealable and temperature controlled.
  • Effective leveling agents have good wetting, emulsifying and dispersing properties and will prevent redeposition. A leveling agent that promotes maximum coverage and color yield is also desirable. Leveling agents particularly suited for high temperature polyester dyeing will generally be suitable for the present invention. Effective leveling agents can also inhibit cationic dye from staining and settling on the walls of stainless steel equipments.
  • the dye removal composition comprises an aqueous solution of at least one leveling agent. Suitable leveling agents include anionic leveling agents, nonionic leveling agents and mixtures thereof.
  • the dye removal composition may further comprise leveling carriers, scouring agents and mixtures thereof. In a particular embodiment of the invention, the scouring agent or wetting agent is nonionic. In another embodiment of the invention, the leveling carrier comprises a nonionic leveling carrier.
  • suitable leveling agents include those that comprise alkyl polyglycol ether, isopropyl alcohol, n-butyl phthalimide or nonyl phenol ethoxylate.
  • suitable leveling carriers include those containing alkyl phthalimide.
  • suitable scouring agents include scouring agents containing polyoxyethene ether or propylene glycol ether.
  • the dye removal composition comprises isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate, and propylene glycol ether.
  • Particular leveling agents that may be used for the present invention include AVOLAN IW LIQUIDTM nonionic leveling agent and scouring agent (Bayer, Pittsburgh, Pa.), DIADAVIN UFNTM nonionic leveling wetting and scouring agent (Bayer, Pittsburgh, Pa.), LEVEGAL EAP-4TM leveling carrier (Bayer, Pittsburgh, Pa.), RAYCAPOL TDA-33 scouring agent (Clariant, Chicago, Ill.), RAYCALEV DTM (leveling agent), CAROLID NOL leveling agent (Bayer, Pittsburgh, Pa.) and RICHLEV D leveling agent (Richchem, High Point, N.C.), BURCO SOUR LFE-810TM scouring agent (Burlington Chemical Co., Burlington, N.C.).
  • the leveling agents When mixed with water or aqueous solution, the leveling agents can be used in weight ratios ranging from (under certain conditions) about 0.5% to as high as about 8.0% of leveling agent:water. However, particularly desirable results are achieved when the leveling agent(s) is present in an amount ranging from about 2.0 wt % to about 8.0 wt % of the total solution of leveling agents.
  • An approximately 4.0 wt % aqueous solution of leveling agent(s) has been found to be particularly suitable for most applications. More particularly, an approximately 4.0 wt % solution comprising propylene glycol ether, isopropyl alcohol, n-butyl phthalimide and nonyl phenol ethoxylate and water has been found to be suitable for most applications.
  • the polyester to be decolorized is separated from any structural elements and placed in a sealable vessel.
  • the polyester may be woven fabric or loose fibers.
  • Water and a dye removal composition comprising at least one leveling agent are added to a vessel at a temperature of about 20° C. to about 25° C.
  • a dye removal composition comprising at least one leveling agent are added to a vessel at a temperature of about 20° C. to about 25° C.
  • any vessel made of a nonreactive material and sealable may be used in place of a standard dyeing vessel.
  • the mixture of the polyester and dye removal composition are heated for a period of about 120 minutes. Because the vessel is sealed, as the temperature increases, there is a corresponding rise in the pressure. Thus, the pressure is higher than the equilibrium pressure of the dye removal composition at the elevated temperature. When the pressure has reached about 28 psi to about 39 psi, more particularly about 33 psi, and the temperature has reached about 135° C. to about 145° C., more particularly 140° C., the vessel is maintained at that pressure and temperature for about 30 minutes to about 60 minutes, more particularly about 45 minutes.
  • the vessel may be agitated during the period when the polyester is first contacted with the dye removal composition, when it is heated, during the holding period when the temperature and pressure are maintained, or any combination of these three. Agitation can be achieved, for example, by rolling the vessel or by continuously pumping the dye removal composition through the polyester.
  • the holding stage is typically followed by a cooling down period of about 20 minutes to about 40 minutes wherein the temperature is decreased to about 20° C. to about 50° C., more particularly 30° C.
  • the mixture should be cooled rapidly to prevent or limit reabsorption of the dye by the polyester.
  • the times and temperatures may vary somewhat depending upon the dyestuff and the leveling agent chosen, but will generally fall within the above ranges for most commonly encountered dyes.
  • the decolorized polyester is then removed from the mixture. Any residual dye removal composition should be removed from the polyester, in order to further limit the chance of reabsorption. This can often be achieved by rinsing thoroughly with water.
  • This cycle may be repeated as needed to remove additional dye from the polyester fiber or fabric.
  • Those with skill in the art will recognize that more intense colors may require additional cycles to sufficiently decolorize the polyester.
  • the method may be carried out as a batch, sequential batch semi-continuous or continuous process.
  • the invention may be used to recycle panel fabric made from polyester.
  • the invention is also useful for recycling panel fabric made from polyester that has already been recycled, such as recycled PET.
  • To recycle panel fabric it should first be separated from any structural elements.
  • the fabric can be, but is not required to be garnetted into loose fibers.
  • any dye should be removed using a dye removal composition comprising an aqueous solution of at least one leveling agent. Once the dye has been removed, the polyester fibers can be recovered. The fibers can be melted and pelletized before being extruded into full-length fiber.
  • Panel fabric may be created by weaving the recycled fiber.
  • the process was carried out in an Ahiba Polymat dyeing machine in sealed vessels. Fifty (50) mL of water was added to an empty vessel. Four (4.0) mL of each of the following chemicals were also added to the vessel: CAROLID NOLTM leveling agent, BURCO SCOUR LFE-810TM scouring agent, and RICHLEV DTM leveling agent. Approximately 5.00 g of polyester was placed into the vessel. Fifty (50) mL of water was added to the vessel to cover the polyester. The vessel was sealed. The vessel was rolled to agitate the mixture. The temperature was raised from room temperature (about 22° C.) to 50° C. The temperature was held at 50° C. for 3.3 minutes.
  • the temperature was raised, over 40 minutes, to 70° C. at a gradient of 0.5.
  • the temperature was then raised to 140° C. at a gradient of 1.5 over a period of 46.7 minutes.
  • the temperature was reduced, over 30.0 minutes, to 50° C. at a gradient of 0.5.
  • the total running time was 116.7 minutes.
  • the process was carried out in an Ahiba Polymat dyeing machine in sealed vessels. Fifty (50) mL of water was added to an empty vessel. Four (4.0) mL of each of the following chemicals were also added to the vessel: AVOLAN IW LIQUIDTM leveling agent, DIADAVIN UFNTM scouring agent, LEVEGAL EAP-4TM leveling carrier and RAYCALEV DTM leveling agent. Approximately 5.00 g of polyester was placed into the vessel. Fifty (50) mL of water was added to the vessel to cover the polyester. The vessel was sealed. The vessel was rolled to agitate the mixture. The temperature was raised from room temperature (about 22° C.) to 50° C. The temperature was held at 50° C. for 3.3 minutes.
  • the temperature was raised, over 40 minutes, to 70° C. at a gradient of 0.5.
  • the temperature was then raised to 135° C. at a gradient of 1.5 over a period of 46.7 minutes.
  • the temperature was reduced, over 30.0 minutes, to 50° C. at a gradient of 0.5.
  • the total running time was 116.7 minutes.

Abstract

Chemical compounds and methods for removing dye from polyester fibers, in particular poly(ethylene terephthalate) (“PET”) fibers, is disclosed. The compounds and methods are particularly useful for removing dye from panel fabric made from recycled PET fibers. The method involves contacting the PET with a dye removal compound in a sealable vessel. The contents of the vessel are agitated and heated to achieve an increase in pressure and temperature. Following a cooling down period, the PET is removed and rinsed with water. The dye removal compound includes an aqueous solution of at least one leveling agent.

Description

    BACKGROUND OF THE INVENTION
  • 1. Field of the Invention
  • This invention relates to chemical compounds and methods for removing dye from polyester fibers, and more particularly to removing dye from panel fabric made from recycled poly(ethylene terephthalate) fibers.
  • 2. Description of Related Art
  • Panel fabric, also known as vertical fabric, is used in furniture upholstery, wall systems and tackboards. Panel fabric is increasingly produced from synthetic materials such as polyester, most commonly PET (poly(ethylene terephthalate)). Panel fabric is replaced periodically and as a result, is often discarded in landfills. Many of the materials used in panel fabric are not biodegradable; thus disposal of it contributes to the environmental problems that arise from the over-use of landfills.
  • Manufacturers of panel fabrics and other materials incorporating PET are concerned about the effect of depletion of petroleum (used to make the polymers in the fabric) and the over-use of landfills on the environment. In an effort to reduce the amount of non-biodegradable waste that finds its way into landfills, some manufacturers use fiber made from recycled PET (often from recycled PET bottles, such as 2-liter soft drink bottles) in panel fabric. However, when the furniture incorporating recycled or virgin panel fabric is discarded or refurbished, the fabric may nevertheless end up in a landfill. Reducing the vast amount of used panel fabric that is discarded annually as landfill waste by finding other uses for such materials is therefore advantageous.
  • However, merely finding other, lower valued uses for the PET in the panel fabric does not alone provide environmental sustainability. As the material is continually downgraded (i.e., used in increasingly less valuable ways), demand for PET for the higher valued uses remains to be satisfied with either virgin PET, or PET that has been recycled from other uses. Accordingly, it is desirable to find a way to avoid downcycling the PET in panel fabric, i.e., to reuse the PET in a way that is economically and environmentally of the same value as the panel fabric itself. Ideally, the PET in the panel fabric would be recycled into fiber that can be reused, e.g., suitable for weaving into new panel fabric. In this way, the material is not only rendered recyclable, but recyclable in a sustainable fashion, decreasing the need for virgin PET or PET recycled from bottles, which can then be put to other uses.
  • Currently, when furniture incorporating panel fabric made from recycled PET is discarded or refurbished, any PET that may be recovered when garnetted into loose fibers is unsuitable for significant reuse in panel fabric and carpet manufacturing. The staple fiber is generally too short to be reused in the yarn spinning process at more than about 3%. If the fibers could be melted, pelletized and extruded into full-length fiber, they could be recycled at about 100%. Unfortunately, the presence of dyes in the fibers makes them difficult to melt and extrude. The dye molecules char and burn at extrusion temperatures, forming a residue that blocks the extrusion spinnerets. As a result, a process capable of removing dye before extrusion is needed.
  • Existing processes may strip or decrease dye levels in polyester, but they do so by breaking the chromophore of the dye. Methods commonly used for color removal employ harsh chemicals like sodium bisulfite, which hydrolyze or oxidize the dye, leaving the decolorized dye in the fiber. This eliminates the color, but leaves the remainder of the dye molecule in the fiber. Thus, when the fiber is melted and extruded, the remaining molecule chars and burns, blocking the extrusion spinnerets.
  • J. R. Aspland, Textile Dyeing and Coloration (American Ass'n of Textile Chemists & Colorists 1997) describes the removal of dye from a polyester fiber at room temperature using methylene chloride. However, this solvent damages the polymer by swelling the PET fiber and solvating the dye. The damage caused is partial hydrolysis of the PET, which causes loss of strength and brittleness in the fibers. For at least this reason, this method is inappropriate for use in manufacturing new carpet or panel fabric. There is therefore a need in the art for a dye removal process that does not damage PET, but effectively removes dye from it.
  • SUMMARY OF THE INVENTION
  • The invention solves some or all of the above mentioned problems by providing methods and compositions for removing dye molecules from polyester, PET in particular. The invention allows the PET to be reused by pelletizing and extruding it into fiber suitable for panel fabric or other applications calling for virgin PET, without disrupting the extrusion process by dye molecule charring.
  • The invention addresses the problem of downcycling the PET in panel fabric by providing a way to use recycled PET that is economically and environmentally of the same value as the panel fabric itself. By using the method of the invention, the PET can be melted, extruded and reused as panel fabric. The invention is an improvement over existing processes because it completely removes the dye molecules from the PET, instead of breaking only the chromophore of the dye. Thus, when the method of the present invention is used, the PET may be melted and extruded, without remaining dye molecules burning or blocking the extrusion spinnerets. Furthermore, the method of the present invention does not damage the PET by swelling.
  • According to one embodiment of the invention, a method is provided for removing dye from polyester fiber or fabric by contacting the polyester with a dye removal composition containing an aqueous solution of at least one leveling agent; heating the mixture of polyester and dye removal composition until it reaches an elevated temperature and pressure level higher than the equilibrium pressure of the dye removal composition at the elevated temperature; cooling the mixture; and removing the decolorized polyester from the mixture.
  • According to another embodiment of the invention, a composition for removing dye from polyester is provided. The composition includes an aqueous solution of about 0.5 wt % to about 8.0 wt % of at least one leveling agent.
  • In another embodiment, the invention relates to a device for removing dye from polyester according to the present invention. The device includes a sealable vessel and a dye removal composition. The dye removal composition includes an aqueous solution of about 0.5 wt % to about 8.0 wt % of at least one leveling agent.
  • The invention is also directed to a method for recycling panel fabric comprising polyester. The method involves removing from the fabric any structural elements, removing the dye from the fabric using a dye removal composition comprising an aqueous solution of at least one leveling agent, recovering the polyester fibers, melting the fibers, pelletizing the melted fiber and extruding the pellets into full-length fiber.
  • In a particular embodiment of the invention, the dye removal composition comprises at least one leveling agent selected from the group consisting of anionic leveling agents, nonionic leveling agents and mixtures thereof.
  • In another particular embodiment of the invention, the dye removal composition further comprises at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers. Leveling agents may perform one or more of these functions in addition to their function as leveling agents.
  • DETAILED DESCRIPTION OF SPECIFIC EMBODIMENTS
  • The invention provides for a method of removing dye molecules from polyester fiber, and is particularly useful with PET fiber. The polyester may be used in the process as woven fabric or, alternatively, garnetted into loose fibers. The polyester is contacted with a dye removal composition comprising an aqueous solution of at least one leveling agent. This may be conveniently done in a standard dyeing vessel commonly used for disperse dyeing of polyester, which is sealable and temperature controlled.
  • Effective leveling agents have good wetting, emulsifying and dispersing properties and will prevent redeposition. A leveling agent that promotes maximum coverage and color yield is also desirable. Leveling agents particularly suited for high temperature polyester dyeing will generally be suitable for the present invention. Effective leveling agents can also inhibit cationic dye from staining and settling on the walls of stainless steel equipments.
  • The dye removal composition comprises an aqueous solution of at least one leveling agent. Suitable leveling agents include anionic leveling agents, nonionic leveling agents and mixtures thereof. The dye removal composition may further comprise leveling carriers, scouring agents and mixtures thereof. In a particular embodiment of the invention, the scouring agent or wetting agent is nonionic. In another embodiment of the invention, the leveling carrier comprises a nonionic leveling carrier.
  • More particularly, examples of suitable leveling agents include those that comprise alkyl polyglycol ether, isopropyl alcohol, n-butyl phthalimide or nonyl phenol ethoxylate. Examples of suitable leveling carriers include those containing alkyl phthalimide. Examples of suitable scouring agents include scouring agents containing polyoxyethene ether or propylene glycol ether. In a most preferred embodiment of the invention, the dye removal composition comprises isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate, and propylene glycol ether.
  • Particular leveling agents that may be used for the present invention include AVOLAN IW LIQUID™ nonionic leveling agent and scouring agent (Bayer, Pittsburgh, Pa.), DIADAVIN UFN™ nonionic leveling wetting and scouring agent (Bayer, Pittsburgh, Pa.), LEVEGAL EAP-4™ leveling carrier (Bayer, Pittsburgh, Pa.), RAYCAPOL TDA-33 scouring agent (Clariant, Chicago, Ill.), RAYCALEV D™ (leveling agent), CAROLID NOL leveling agent (Bayer, Pittsburgh, Pa.) and RICHLEV D leveling agent (Richchem, High Point, N.C.), BURCO SOUR LFE-810™ scouring agent (Burlington Chemical Co., Burlington, N.C.).
  • When mixed with water or aqueous solution, the leveling agents can be used in weight ratios ranging from (under certain conditions) about 0.5% to as high as about 8.0% of leveling agent:water. However, particularly desirable results are achieved when the leveling agent(s) is present in an amount ranging from about 2.0 wt % to about 8.0 wt % of the total solution of leveling agents. An approximately 4.0 wt % aqueous solution of leveling agent(s) has been found to be particularly suitable for most applications. More particularly, an approximately 4.0 wt % solution comprising propylene glycol ether, isopropyl alcohol, n-butyl phthalimide and nonyl phenol ethoxylate and water has been found to be suitable for most applications.
  • According to this invention, the polyester to be decolorized is separated from any structural elements and placed in a sealable vessel. The polyester may be woven fabric or loose fibers. Water and a dye removal composition comprising at least one leveling agent are added to a vessel at a temperature of about 20° C. to about 25° C. Those with skill in the art will understand that any vessel made of a nonreactive material and sealable may be used in place of a standard dyeing vessel.
  • The mixture of the polyester and dye removal composition are heated for a period of about 120 minutes. Because the vessel is sealed, as the temperature increases, there is a corresponding rise in the pressure. Thus, the pressure is higher than the equilibrium pressure of the dye removal composition at the elevated temperature. When the pressure has reached about 28 psi to about 39 psi, more particularly about 33 psi, and the temperature has reached about 135° C. to about 145° C., more particularly 140° C., the vessel is maintained at that pressure and temperature for about 30 minutes to about 60 minutes, more particularly about 45 minutes.
  • The vessel may be agitated during the period when the polyester is first contacted with the dye removal composition, when it is heated, during the holding period when the temperature and pressure are maintained, or any combination of these three. Agitation can be achieved, for example, by rolling the vessel or by continuously pumping the dye removal composition through the polyester.
  • The holding stage is typically followed by a cooling down period of about 20 minutes to about 40 minutes wherein the temperature is decreased to about 20° C. to about 50° C., more particularly 30° C. The mixture should be cooled rapidly to prevent or limit reabsorption of the dye by the polyester.
  • The times and temperatures may vary somewhat depending upon the dyestuff and the leveling agent chosen, but will generally fall within the above ranges for most commonly encountered dyes.
  • The decolorized polyester is then removed from the mixture. Any residual dye removal composition should be removed from the polyester, in order to further limit the chance of reabsorption. This can often be achieved by rinsing thoroughly with water.
  • This cycle may be repeated as needed to remove additional dye from the polyester fiber or fabric. Those with skill in the art will recognize that more intense colors may require additional cycles to sufficiently decolorize the polyester. The method may be carried out as a batch, sequential batch semi-continuous or continuous process.
  • The invention may be used to recycle panel fabric made from polyester. The invention is also useful for recycling panel fabric made from polyester that has already been recycled, such as recycled PET. To recycle panel fabric, it should first be separated from any structural elements. The fabric can be, but is not required to be garnetted into loose fibers. In order to fully recycle the panel fabric so that it can be used again as panel fabric or some other product of similar economic and environmental value, any dye should be removed using a dye removal composition comprising an aqueous solution of at least one leveling agent. Once the dye has been removed, the polyester fibers can be recovered. The fibers can be melted and pelletized before being extruded into full-length fiber. Panel fabric may be created by weaving the recycled fiber.
  • The invention can be more clearly understood by reference to the following examples, which are not intended to limit the scope of the invention in any way.
  • EXAMPLE 1
  • The process was carried out in an Ahiba Polymat dyeing machine in sealed vessels. Fifty (50) mL of water was added to an empty vessel. Four (4.0) mL of each of the following chemicals were also added to the vessel: CAROLID NOL™ leveling agent, BURCO SCOUR LFE-810™ scouring agent, and RICHLEV D™ leveling agent. Approximately 5.00 g of polyester was placed into the vessel. Fifty (50) mL of water was added to the vessel to cover the polyester. The vessel was sealed. The vessel was rolled to agitate the mixture. The temperature was raised from room temperature (about 22° C.) to 50° C. The temperature was held at 50° C. for 3.3 minutes. Next, the temperature was raised, over 40 minutes, to 70° C. at a gradient of 0.5. The temperature was then raised to 140° C. at a gradient of 1.5 over a period of 46.7 minutes. Finally, the temperature was reduced, over 30.0 minutes, to 50° C. at a gradient of 0.5. The total running time was 116.7 minutes.
  • The process was carried out in an Ahiba Polymat dyeing machine in sealed vessels. Fifty (50) mL of water was added to an empty vessel. Four (4.0) mL of each of the following chemicals were also added to the vessel: AVOLAN IW LIQUID™ leveling agent, DIADAVIN UFN™ scouring agent, LEVEGAL EAP-4™ leveling carrier and RAYCALEV D™ leveling agent. Approximately 5.00 g of polyester was placed into the vessel. Fifty (50) mL of water was added to the vessel to cover the polyester. The vessel was sealed. The vessel was rolled to agitate the mixture. The temperature was raised from room temperature (about 22° C.) to 50° C. The temperature was held at 50° C. for 3.3 minutes. Next, the temperature was raised, over 40 minutes, to 70° C. at a gradient of 0.5. The temperature was then raised to 135° C. at a gradient of 1.5 over a period of 46.7 minutes. Finally, the temperature was reduced, over 30.0 minutes, to 50° C. at a gradient of 0.5. The total running time was 116.7 minutes.
  • The foregoing description is provided for describing various embodiments and structures relating to the invention. Various modifications, additions and deletions may be made to these embodiments and/or structures without departing from the scope and spirit of the invention.

Claims (55)

1. A method for removing dye from polyester comprising:
a) contacting the polyester with a dye removal composition comprising an aqueous solution of at least one leveling agent to form a mixture;
b) heating the mixture until it reaches an elevated temperature and a pressure higher than the equilibrium pressure of the dye removal composition at the elevated temperature;
c) maintaining the mixture at the elevated temperature and pressure for a time interval sufficient to at least partially remove dye from the polyester;
d) cooling the mixture;
e) separating the polyester from the mixture; and
f) removing any residual dye removal composition from the polyester.
2. The method of claim 1 wherein the dye removal composition further comprises at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers.
3. The method of claim 1 wherein the leveling agent is selected from the group consisting of anionic leveling agents, nonionic leveling agents and mixtures thereof.
4. The method of claim 3 wherein the leveling agent is selected from the group consisting of alkyl polyglycol ether, isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate and combinations thereof.
5. The method of claim 2 wherein the scouring agent or wetting agent is nonionic.
6. The method of claim 5 wherein the nonionic scouring agent or wetting agent is selected from the group consisting of polyoxyethene ethers.
7. The method of claim 2 wherein the leveling carrier comprises a nonionic leveling carrier.
8. The method of claim 7 wherein the nonionic leveling carrier comprises alkyl phthalimide.
9. The method of claim 2 wherein the dye removal composition comprises isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate, propylene glycol ether and combinations thereof.
10. The method of claim 1 wherein the dye removal composition comprises an aqueous solution of about 0.5 wt % to about 8.0 wt % of leveling agent, based on the total dye removal composition.
11. The method of claim 10 wherein the dye removal composition comprises an aqueous solution of about 2.0 wt % to about 8.0 wt %/o of leveling agent, based on the total dye removal composition.
12. The method of claim 11 wherein the dye removal composition comprises an aqueous solution of about 4.0 wt % to about 8.0 wt % leveling agent, based on the total dye removal composition.
13. The method of claim 1 wherein the mixture is agitated for about 120 minutes during one or more of the contacting, heating or maintaining steps.
14. The method of claim 1 wherein the mixture is maintained at a pressure of about 28 psi to about 39 psi.
15. The method of claim 14 wherein the mixture is maintained at a pressure of about 33 psi.
16. The method of claim 1 wherein the mixture is heated to a temperature of from about 135° C. to about 145° C.
17. The method of claim 16 wherein the mixture is maintained at the elevated temperature about 140° C.
18. The method of claim 1 wherein the mixture is maintained at the elevated temperature for a period of about 30 minutes to about 60 minutes.
19. The method of claim 18 wherein the mixture is maintained at the elevated temperature for about 45 minutes.
20. The method of claim 1 wherein the mixture is cooled over a period of about 20 minutes to about 40 minutes.
21. The method of claim 1 wherein the mixture is cooled to a temperature of about 20° C. to about 50° C.
22. The method of claim 21 wherein the mixture is cooled to a temperature of about 30° C.
23. The method of claim 1 wherein the polyester comprises polyester obtained from panel fabric.
24. The method of claim 23 wherein the panel fabric has been garnetted into loose fibers.
25. The method of claim 1 wherein the method is carried out in a sealable vessel.
26. The method of claim 1 wherein the method is carried out as a batch process.
27. The method of claim 1 wherein the polyester comprises poly(ethylene terephthalate) (“PET”).
28. A method for removing dye from PET comprising:
a) contacting the PET with a dye removal composition comprising an aqueous solution of one or more of propylene glycol ether, isopropyl alcohol, n-butyl phthalimide and nonyl phenol ethoxylatein to form a mixture;
b) heating the mixture for about 120 minutes;
c) maintaining the temperature of the mixture at about 140° C. and the pressure at about 33 psi for a time sufficient to at least partially remove dye from the PET;
d) cooling the mixture to 30° C. over a period of about 20 minutes to 40 minutes;
e) separating the PET from the mixture; and
f) rinsing the PET with water.
29. A composition for removing dye from polyester comprising an aqueous solution of about 2.0 wt % to about 8.0 wt % of at least one leveling agent, based on the total composition.
30. The composition of claim 29 wherein the composition comprises an aqueous solution of about 4.0 wt % to about 8.0 wt % of leveling agent, based on the total composition.
31. The composition of claim 29 further comprising at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers.
32. The composition of claim 29 further comprising at least one leveling agent selected from the group consisting of anionic leveling agents, nonionic leveling agents and mixtures thereof.
33. The composition of claim 32 wherein the leveling agent is selected from the group consisting of alkyl polyglycol ether, isopropyl alcohol, n-butyl phthalimide and nonyl phenol ethoxylate.
34. The composition of claim 31 wherein the scouring agent or wetting agent is nonionic.
35. The composition of claim 34 wherein the nonionic scouring agent or wetting agent is selected from the group consisting of polyoxyethene ethers.
36. The composition of claim 31 wherein the leveling carrier comprises a nonionic leveling carrier.
37. The composition of claim 36 wherein the nonionic leveling carrier comprises alkyl phthalimide.
38. The composition of claim 31 wherein the composition comprises isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate, and propylene glycol ether.
39. The composition of claim 29 wherein the polyester comprises PET.
40. A device for removing dye from polyester, comprising:
a sealable vessel; and
a dye removal composition disposed therein, the dye removal composition comprising an aqueous solution of about 2.0 wt % to about 8.0 wt % of at least one leveling agent, based on the total dye removal composition.
41. The device of claim 40, wherein the dye removal composition comprises an aqueous solution of about 4.0 wt % to about 8.0 wt % leveling agent.
42. The device of claim 40 wherein the dye removal composition further comprises at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers.
43. The device of claim 40 wherein the dye removal composition comprises at least one leveling agent selected from the group consisting of anionic leveling agents, nonionic leveling agents and mixtures thereof.
44. The device of claim 43 wherein the dye removal composition comprises at least one leveling agent selected from the group consisting of alkyl polyglycol ether, isopropyl alcohol, n-butyl phthalimide and nonyl phenol ethoxylate.
45. The device of claim 42 wherein the scouring agent or wetting agent is nonionic.
46. The device of claim 45 wherein the nonionic scouring agent or wetting agent is selected from the group consisting of polyoxyethene ethers.
47. The device of claim 42 wherein the leveling carrier comprises a nonionic leveling carrier.
48. The device of claim 47 wherein the nonionic leveling carrier comprises alkyl phthalimide.
49. The device of claim 40 wherein the dye removal composition comprises one or more of isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate and propylene glycol ether.
50. The device of claim 40 wherein the polyester comprises PET.
51. A method for recycling panel fabric comprising polyester, the method comprising:
a) removing from the fabric any structural elements;
b) removing dye from the fabric using the method of claim 1;
c) recovering the polyester;
d) melting the polyester;
e) pelletizing the melted polyester; and
f) extruding the resulting pellets into full-length fiber.
52. The method of claim 51 wherein the contacting takes place in a sealable vessel and the residual dye removal composition is removed by rinsing with water.
53. The method of claim 51 wherein the dye removal composition further comprises at least one chemical selected from the group consisting of scouring agents, wetting agents and leveling carriers.
54. The method of claim 53 wherein the dye removal composition comprises isopropyl alcohol, n-butyl phthalimide, nonyl phenol ethoxylate, and propylene glycol ether.
55. The method of claim 51 wherein the polyester comprises PET.
US10/505,248 2002-02-01 2003-01-31 Chemical compounds and methods for removing dye Abandoned US20050198742A1 (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040082672A1 (en) * 2002-10-16 2004-04-29 Fuquan Zeng Process for recyling colored thermoplastic molded articles
US20090130443A1 (en) * 2007-11-16 2009-05-21 Arnold Lustiger Fiber pellets, method of making, and use in making fiber reinforced polypropylene composites
US10047209B2 (en) 2012-09-24 2018-08-14 Radco Infusion Technologies, Inc. Removal of color from thermoplastics
WO2021055111A1 (en) * 2019-09-09 2021-03-25 Revolaze, LLC Improved scouring process for ring dyed denim fabric and material produced thereof
TWI750456B (en) * 2019-02-22 2021-12-21 南亞塑膠工業股份有限公司 A kind of decolorization method for dyed polyester
CN114960172A (en) * 2021-02-24 2022-08-30 南亚塑胶工业股份有限公司 Method for decoloring fiber cloth

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI481762B (en) * 2013-09-04 2015-04-21 Far Eastern New Century Corp Decolorization of Polyester Fibers Dyed by Dye
CN112219470A (en) * 2020-09-29 2021-01-15 安徽灵杨机械装备股份有限公司 Guiding mechanism of seeder and seeder

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3582255A (en) * 1967-05-26 1971-06-01 Sandoz Ltd Process for stripping dyeings and prints from hydrophobic fibres
US4227881A (en) * 1978-11-17 1980-10-14 Royce Chemical Company New process of color stripping dyed textile fabric
US4435473A (en) * 1980-04-02 1984-03-06 Ppg Industries, Inc. Aqueous peroxide emulsion for use with glass fibers
US4783193A (en) * 1985-06-10 1988-11-08 Laury Pensa Composition and process for stripping color from synthetic polymer products
US4943299A (en) * 1987-10-09 1990-07-24 Bayer Aktiengesellschaft Levelling agents for disperse dyeing of polyester: ethoxylate or propoxylate of substituted phenol, emulsifier and carrier
US5152989A (en) * 1989-12-08 1992-10-06 Aps Apotheker H. Starke Gmbh Bath additive and its use
US5228953A (en) * 1990-10-30 1993-07-20 Bk Ladenburg Gmbh Gesellschaft Fur Chemische Erzeugnisse Deinking waste paper using a polyglycol and a phosphoric ester mixture
US5660684A (en) * 1994-09-12 1997-08-26 Ppg Industries, Inc. Deinking electrostatic waste paper
US5900392A (en) * 1998-07-24 1999-05-04 Loeffler Chemical Corporation Aqueous belt lubricant composition based on fatty alkyl propylene tettramines and fatty alcohol polyglycol ethers and method for lubricating belt conveyor systems
US5972049A (en) * 1998-01-28 1999-10-26 Sybron Chemicals Inc. Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles
US6313182B1 (en) * 1999-05-04 2001-11-06 Air Products And Chemicals, Inc. Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1445168A (en) * 1973-11-14 1976-08-04 Horizons Research Inc Process for recovery of clean polyester materials
EP0131558A3 (en) * 1983-07-06 1986-06-11 Bergvik Kemi AB Dispersing agent
US4722738A (en) * 1984-02-27 1988-02-02 Crucible Chemical Company Process to decolorize dye composition and method of use thereof for coloring thermoplastic articles
ATE190087T1 (en) * 1994-08-30 2000-03-15 Procter & Gamble PHOTO BLEACHING IMPROVED BY CHELATES
US6048367A (en) * 1997-12-23 2000-04-11 Novo Nordisk A/S Process for removal of excess dye from printed or dyed fabric or yarn

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3582255A (en) * 1967-05-26 1971-06-01 Sandoz Ltd Process for stripping dyeings and prints from hydrophobic fibres
US4227881A (en) * 1978-11-17 1980-10-14 Royce Chemical Company New process of color stripping dyed textile fabric
US4435473A (en) * 1980-04-02 1984-03-06 Ppg Industries, Inc. Aqueous peroxide emulsion for use with glass fibers
US4783193A (en) * 1985-06-10 1988-11-08 Laury Pensa Composition and process for stripping color from synthetic polymer products
US4943299A (en) * 1987-10-09 1990-07-24 Bayer Aktiengesellschaft Levelling agents for disperse dyeing of polyester: ethoxylate or propoxylate of substituted phenol, emulsifier and carrier
US5152989A (en) * 1989-12-08 1992-10-06 Aps Apotheker H. Starke Gmbh Bath additive and its use
US5228953A (en) * 1990-10-30 1993-07-20 Bk Ladenburg Gmbh Gesellschaft Fur Chemische Erzeugnisse Deinking waste paper using a polyglycol and a phosphoric ester mixture
US5660684A (en) * 1994-09-12 1997-08-26 Ppg Industries, Inc. Deinking electrostatic waste paper
US5972049A (en) * 1998-01-28 1999-10-26 Sybron Chemicals Inc. Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles
US5900392A (en) * 1998-07-24 1999-05-04 Loeffler Chemical Corporation Aqueous belt lubricant composition based on fatty alkyl propylene tettramines and fatty alcohol polyglycol ethers and method for lubricating belt conveyor systems
US6313182B1 (en) * 1999-05-04 2001-11-06 Air Products And Chemicals, Inc. Acetylenic diol ethylene oxide/propylene oxide adducts and processes for their manufacture

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040082672A1 (en) * 2002-10-16 2004-04-29 Fuquan Zeng Process for recyling colored thermoplastic molded articles
US20090130443A1 (en) * 2007-11-16 2009-05-21 Arnold Lustiger Fiber pellets, method of making, and use in making fiber reinforced polypropylene composites
US8211341B2 (en) 2007-11-16 2012-07-03 Exxonmobil Research And Engineering Company Fiber pellets method of making, and use in making fiber reinforced polypropylene composites
US10047209B2 (en) 2012-09-24 2018-08-14 Radco Infusion Technologies, Inc. Removal of color from thermoplastics
TWI750456B (en) * 2019-02-22 2021-12-21 南亞塑膠工業股份有限公司 A kind of decolorization method for dyed polyester
WO2021055111A1 (en) * 2019-09-09 2021-03-25 Revolaze, LLC Improved scouring process for ring dyed denim fabric and material produced thereof
CN114960172A (en) * 2021-02-24 2022-08-30 南亚塑胶工业股份有限公司 Method for decoloring fiber cloth

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