EP4004093A1 - Procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique ; matériau polymère polaire synthétique coloré et article associé - Google Patents

Procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique ; matériau polymère polaire synthétique coloré et article associé

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Publication number
EP4004093A1
EP4004093A1 EP20740349.4A EP20740349A EP4004093A1 EP 4004093 A1 EP4004093 A1 EP 4004093A1 EP 20740349 A EP20740349 A EP 20740349A EP 4004093 A1 EP4004093 A1 EP 4004093A1
Authority
EP
European Patent Office
Prior art keywords
polar
polymer material
synthetic
synthetic polar
colored
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.)
Pending
Application number
EP20740349.4A
Other languages
German (de)
English (en)
Inventor
Hendre Vos
Bernd Robertz
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.)
Smart Coloring GmbH
Original Assignee
Smart Coloring GmbH
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
Priority claimed from EP19188085.5A external-priority patent/EP3770318A1/fr
Priority claimed from EP19188098.8A external-priority patent/EP3770208B1/fr
Application filed by Smart Coloring GmbH filed Critical Smart Coloring GmbH
Publication of EP4004093A1 publication Critical patent/EP4004093A1/fr
Pending legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/81—General 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 dyes dissolved in inorganic solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/90—General 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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/90—General 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 dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General 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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/131—Fugitive dyeing or stripping dyes with acids or bases
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/132—Fugitive dyeing or stripping dyes with oxidants
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/134—Fugitive dyeing or stripping dyes with reductants
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/15—Locally discharging the dyes
    • D06P5/158—Locally discharging the dyes with other compounds
    • 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
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/04—Homopolymers or copolymers of ethene
    • C08J2323/06—Polyethene
    • 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
    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2423/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2423/04—Homopolymers or copolymers of ethene
    • C08J2423/08—Copolymers of ethene
    • 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
    • C08J2429/00—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 alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2429/02—Homopolymers or copolymers of unsaturated alcohols
    • C08J2429/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • 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
    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • 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
    • C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2467/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
    • 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
    • C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2475/04—Polyurethanes
    • 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
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • 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
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2477/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • 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
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2477/06—Polyamides derived from polyamines and polycarboxylic acids
    • 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 relates to a method for reversible and selective coloring of synthetic polar-polymer material, to a colored synthetic polar-polymer material, and to an article comprising at least one colored synthetic polar-polymer material.
  • US 3 663 262 A refers to a process for repeatedly tinting and changing the color of solid materials which comprises applying a polymeric composition to the material and thereafter contacting the treated material with a dye which has a higher affinity for the polymeric composition than the material. In this manner the dye is temporarily fixed on the material and can be removed by washing in a detergent solution. The dyeing and removing steps can be repeated. The dye is added on top of the outer surface like a paint and formes a separate dye layer.
  • US 3 663 262 A refers to a process wherein on top of the outer surface of a polymer material a dye is applied that means a dye layer is formed on the outer surface of a polymer material like painting.
  • CN 104 841 389 B refers to a preparation method of an organic/inorganic hybrid material POSS-PDMAEMA two-phase adsorbed organic dye.
  • a POSS-containing organic/inorganic hybrid material POSS-PDMAEMA used by the method has amphipathy and can be self- assembled into micelles in an aqueous solution and under suitable conditions, an organic dye is loaded to the interior of the micelles, and the purpose of two-phase adsorption of the organic dye is achieved.
  • YAOAGIRI RACHURI ET AL. "Selective and reversible adsorption of cationic dyes by mixed ligand Zn(ll) coordination polymers synthesized by reactant ration modulation", DALTON TRANSACTIONS, vol. 47, 6 December 2017 (2017-12-06), pages 898-908.
  • US 2014/127477 A1 refers to systems and methods in which composite solids such as dyed fibers or fabrics are produced by reversibly generating permeable regions within a heterogeneous solid. Permeating substances are trapped within the heterogeneous solid on reversal of the permeability to form a composite solid, within which the permeating substances are protected from environmental factors.
  • US 2016/102430 A1 refers to systems, methods, and devices that dispense microdroplets of dye onto individual filaments or fibers and infuse them into the interior of such filaments and/or fibers in a highly controlled manner. Control of dye dispensing permits changing the dye applied to a fiber during a dyeing operation, and supports the generation of patterns in woven products via the dyeing process. The resulting systems and methods require much less water and generate much less waste than conventional dyeing processes.
  • VESNA V. PANIC ET AL. "Adsorption of azo dyes on polymer materials", HEM. INO., vol. 67, no. 6, 2013, pages 881-900.
  • the dyeing of plastics to colored polymer components is usually achieved by using color master batches, colored micro granules, so-called dry liquid colors or liquid colors.
  • Colored polymer components can for example be produced from color master batch concentrates blended into a polymer prior to molding or extruding or pre-colored polymers via melt blending/ compounding.
  • the selection of one dyeing method over the other may vary based on economics, secondary operations and specific requirements of the end application.
  • the pigment or dye When dyeing with a master batch, in an upstream step, the pigment or dye is first dispersed or dissolved in a polymeric carrier with the addition of dispersants and if necessary or required further additives.
  • a polymeric carrier In order to achieve a fine and homogeneous distribution of the pigments or dyes, twin-screw extruders are often used to produce the master batches. Separate master batches are required for each different color and - depending on the carrier selected and the final application - for the different plastics that are to be colored with the master batch. This leads to an inefficient process, especially with small batch sizes and frequent color changes.
  • plastics processors The most common method used by plastics processors is the use of concentrated pigments dispersed into a polymer carrier resin by molding process. During molding the master batch is let down into natural resin as it is feed into the extruder at a predefined ratio to achieve the desired color.
  • the processing of the master batches also has major disadvantages for the plastics processor. On the one hand this is connected with a complex storage of different color master batches, on the other hand frequent color changes on the extrusion or injection molding machine lead to an inefficient process due to material losses, cleaning processes and downtimes.
  • the selection of the color pigment depends, among other things, on the desired color, the polymer carrier to be used, the application and the associated requirements, but also on the further processing conditions at the plastics processor- e.g. conventional injection molding or hot runner technology.
  • Hot runner technology is characterized by the fact that the gate system is heated separately from the rest of the mold in order to maintain the flowability of the plastic melt at a constant level. The melt and thus also the colorants are exposed to a higher thermal load which further restricts the choice of pigments.
  • polar polymer materials comprising a substantial content of non-polar polymers, such as polyalkylenes, polyethylene (PE), polypropylene (PP), polybutylene (PB), polystyrene or mixtures thereof.
  • non-polar polymers such as polyalkylenes, polyethylene (PE), polypropylene (PP), polybutylene (PB), polystyrene or mixtures thereof.
  • polar polymer materials comprising co-polyester, co-polycarbonates, acrylonitrile-butadiene-styrene, polyamide, polyurethane, polyalkyl(meth)acrylate, allyldiglycol carbonate, styrene copolymers or mixtures thereof, or in addition non-polar polymers, such as polyalkylenes, polyethylene (PE), polypropylene (PP), polybutylene (PB) or mixtures thereof.
  • PE polyethylene
  • PP polypropylene
  • PB polybutylene
  • the plastic parts, foils, etc. produced in this way can only be recycled at great expense after application (end-of-life).
  • colored polymer articles recycling may be connected to separating the articles according to their color, in order to achieve high quality recycled material.
  • decolorization processes may be oxidation or reduction process, wherein the used dyes are decolorized by chemical modifying the dye such as destroying the conjugated double-bond system. This has the drawback that the destroyed dye compounds remain in the polymer material and the used oxidation or reduction agents are very aggressive and used in high amounts, which is not environmentally friendly.
  • Recyclers may counter this with the addition of other colorants such as titanium dioxide.
  • other colorants such as titanium dioxide.
  • this impairs the physical properties and processability of the plastics, which further restricts their range of application.
  • further recycling is made much more difficult because additional colorants are added with each cycle, further impairing the physical properties of the polymer.
  • the aqueous dispersed dyeing solution comprises: - at least one organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol,
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a temperature in the range of about > 30 °C to about ⁇ 150 °C, and optionally a pH in the range of about > 2.5 and ⁇ 7 and wherein the dispersing agent is selected different from the solubilizer.
  • the synthetic polar-polymer material before dyeing may have for example a transulcent white like frosted glass color or colour less.
  • the basic idea of method for reversible and selective dyeing synthetic polar-polymer material is to use at least one organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol.
  • the dye have the ability for dyeing / coloring at least an outer layer of the synthetic polar-polymer material.
  • the organic aromatic dye may have the ability to migrate into the synthetic polar-polymer material and therefore dyeing the synthetic polar-polymer material.
  • a migration of the organic aromatic dye into the synthetic polar-polymer material may also allow a migration of the organic aromatic dye out of the colored synthetic polar-polymer material. Therefore a dyeing of the colored material may be possible.
  • the organic aromatic dye preferably has a rather planar structure and preferably comprises at least one free rotation center outside the planar structure.
  • the ligands and/or remnants may be as freely movable as possible around a center of rotation.
  • This may give the organic aromatic dye the ability to adapt its shape to the environment given by the matrix of the synthetic polar-polymer material.
  • the organic aromatic dye may not comprise a spiro-center and/or the organic aromatic dye may not comprise a large moiety that is rotation-impaired.
  • a large moiety that is rotation impaired may mean that the molecular weight of this rotation impaired moiety is about 350 g/mol +/- 10%.
  • the object of the present invention is not to dye through.
  • the object of the present invention is rather to dye a defined thickness of the outer surface that means the dye concentration is enriched in a defined thickness of an outer surface.
  • thin but deeply colored layers of color are obtained.
  • a color change from translucent like frosted glass to deep blue may be achieved with a significant low amount of dye, because a defined thickness of the outer layer is colored and need not be colored through.
  • the synthetic polar-polymer material may not being dissolved in the aqueous dispersed dyeing solution for coloring. It may be preferred that the synthetic polar-polymer material can be an article or a part of an article, which is not dissolved in the aqueous dispersed dyeing solution for coloring.
  • the dyeing process may be broken down into several sub-steps. These include the absorption of the dye on the polymer surface, the adsorption of the dye into the polymer outer surface or outer surface of a plastic article, like a bottle, and the diffusion of the dye into the outer layer.
  • the diffusion speed is speed-limiting for the coloring, so that high dye concentrations may present in the polymer surface but near the outer-surface.
  • the dye may be deposited in the “droplets (domains) of the polar polymer / oligomer / additive and may be in the interfaces between the polar and non-polar areas.
  • the dye or dyes can be removed from for example from intact products without destroying them.
  • the articles for decolorization may be destroyed by for example shredding or powdering.
  • plastic-affine and dye- affine additives may be used, which displace the dye from the plastic and bring it into the extraction medium.
  • Additives useful for decolorization are compounds that reduce the glass point of the polymeric material to be decolorized, swelling additives or organic solvents that increase the chain spacing of the polymeric material to be decolorized like carrier, plasticizer, or DMF may be useful for use. Adjustment of the pH-value, which may increases the solubility of the dye in the extraction medium may be useful for use.
  • the aqueous dispersed dyeing solution comprises at least one dispersing agent for dispersing the organic aromatic dye in the aqueous solution.
  • the organic aromatic dye may only be partially soluble in the aqueous solution.
  • the dispersing agent may enhance the stability of the aqueous dispersed dyeing solution by distributing the organic aromatic dye in the phase of the aqueous solution.
  • the aqueous dispersed dyeing solution optionally may comprise at least one solubilizer.
  • the solubilizer may enhance the solubility of the organic aromatic dye in the aqueous solution.
  • the amount of molecularly solved organic aromatic dye may be enhanced by the solubilizer. Therefore, the solubilizer may improve the result of the dyeing process.
  • the outer surface of the synthetic polar-polymer material is exposed to the aqueous dispersed dyeing solution, wherein the aqueous dispersed dyeing solution has a temperature in the range of about > 30 °C to about ⁇ 150 °C.
  • the synthetic polar-polymer material is colored.
  • the colorization process may be carried out in an open reactor without pressure.
  • temperatures about > 90 °C, preferably about > 100 °C, of the aqueous dispersed dyeing solution the colorization process may be carried out in a closed reactor under pressure.
  • the aqueous dispersed dyeing solution comprises:
  • At least one acid preferably a C2 to Cs organic acid, more preferred acetic acid
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably has a temperature in the range of about > 60 °C to about ⁇ 100 °C and wherein the dispersing agent is selected different from the solubilizer.
  • the method for reversible and selective dyeing a synthetic polar-polymer material comprises the steps:
  • the aqueous dispersed dyeing solution comprises:
  • At least one acid preferably a C2 to Cs organic acid, more preferred acetic acid
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably has a temperature in the range of about > 60 °C to about ⁇ 100 °C, and wherein the dispersing agent is selected different from the solubilizer; and wherein the synthetic polar-polymer material contains > 5 wt- % to about ⁇ 99.5 wt.-%, preferably > 10 wt.-% to about ⁇ 99.5 wt.-%, more preferably > 15 wt- % to about ⁇ 99.5 wt.-%, further preferably about > 90 wt.-% to about ⁇ 99.5 wt.-% of the synthetic non-polar-polymers, also named non-polar-polymer, selected from the group comprising polyalky
  • aqueous dispersed dyeing solution comprises:
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C and optionally a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and wherein the dispersing agent is selected different from the solubilizer.
  • the polar additive may be solid at 23 °C.
  • the polar additive may be not a dye.
  • the polar additive may be solid at 23 °C and is not a dye.
  • the polar additive may be solid at 23 °C and is not a dye, is selected different from the dispersing agent and is selected different from the solubilizer.
  • the polar additive doesn’t coloring/dyeing the synthetic polar-polymer material.
  • the aqueous dispersed dyeing solution may not comprise a glycol ether, glycol and/or butanediol.
  • the method for reversible and selective dyeing a synthetic polar-polymer material wherein the synthetic polar-polymer material contains > 0 wt.-% to about ⁇ 99.5 wt.-% of a synthetic non-polar-polymer, based on the total weight of the synthetic polar-polymer material, the method may comprise the steps:
  • the aqueous dispersed dyeing solution comprises: - at least one organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol,
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C, and optionally a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6 and wherein the dispersing agent is selected different from the solubilizer.
  • the method for reversible and selective dyeing a synthetic polar-polymer material comprises the steps:
  • the aqueous dispersed dyeing solution comprises:
  • At least one acid preferably a C2 to Cs organic acid, more preferred acetic acid
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C and wherein the dispersing agent is selected different from the solubilizer.
  • the method for reversible and selective dyeing a synthetic polar-polymer material wherein the synthetic polar-polymer material contains > 5 wt.-% to about ⁇ 99.5 wt.-% of a synthetic non-polar-polymer, preferably > 10 wt- % to about ⁇ 99.5 wt.-% of a synthetic non-polar-polymer, more preferably > 15 wt.-% to about ⁇ 99.5 wt.-% of a synthetic non-polar-polymer, further preferably about > 90 wt.-% to about ⁇ 99.5 wt.-% of a synthetic non-polar-polymer based on the total weight of the synthetic polar-polymer material, the method may comprise the steps:
  • the aqueous dispersed dyeing solution comprises:
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C, and optionally a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6 and wherein the dispersing agent is selected different from the solubilizer.
  • non-polar polymers also named synthetic non-polar- polymer
  • the synthetic polar-polymer material contains > 5 wt.-% to about ⁇ 99.5 wt.-%, preferably > 10 wt.-% to about ⁇ 99.5 wt.-%, more preferably > 15 wt.-% to about ⁇ 99.5 wt.-%, further preferably about > 90 wt.-% to about ⁇ 99.5 wt.-% of the synthetic non-polar-polymers, also named non-polar-polymer, selected from the group comprising polyalkylenes, polyethylene (PE), polypropylene (PP), polybutylene (PB), wherein the weight amount of the synthetic non-polar-polymer is based on the total weight of the synthetic polar-polymer material.
  • non-polar-polymer selected from the group comprising polyalkylenes, polyethylene (PE), polypropylene (PP), polybutylene (PB), wherein the weight amount of the synthetic non-polar-polymer is based on the total weight of the synthetic polar
  • the synthetic polar-polymer material that is colored comprises at least one synthetic polar-component, wherein the synthetic polar-component comprises:
  • polar-additive having a Mw about > 70 and ⁇ 600 g/mol, wherein the polar- additive is selected different to the organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol.
  • the weight % of the non-polar-polymer, the synthetic polar- polymer, the synthetic polar-oligomer, the polar-additive are based on the total weight amount of said composition, and wherein the weight amounts are selected such that it doesn’t exceed 100 wt.-%;
  • the polar-additive is selected different to the organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol.
  • the synthetic polar-polymer material that is colored comprises at least one synthetic polar-component, wherein the synthetic polar-component comprises:
  • polar-additive having a Mw about > 70 and ⁇ 600 g/mol, wherein the polar- additive is selected different to the organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol, and
  • aqueous dispersed dyeing solution comprises:
  • At least one acid preferably a C2 to Cs organic acid, more preferred acetic acid
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C and wherein the dispersing agent is selected different from the solubilizer.
  • the method for reversible and selective dyeing a synthetic polar-polymer material comprises the steps:
  • the synthetic polar-polymer material that is colored comprises at least one synthetic polar-component, wherein the synthetic polar-component comprises:
  • aqueous dispersed dyeing solution comprises:
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C and optionally a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and wherein the dispersing agent is selected different from the solubilizer.
  • polar-additive having a Mw about > 70 and ⁇ 600 g/mol, wherein the polar- additive is selected different to the organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol, and
  • aqueous dispersed dyeing solution comprises:
  • At least one acid preferably a C2 to Cs organic acid, more preferred acetic acid
  • the aqueous dispersed dyeing solution exposing the synthetic polymer material has a pH in the range of about > 2.5 and ⁇ 7, preferably a pH in the range of about > 3.4 and about ⁇ 6, and a temperature in the range of about > 30 °C to about ⁇ 150 °C, preferably a temperature in the range of about > 60 °C to about ⁇ 100 °C and wherein the dispersing agent is selected different from the solubilizer.
  • the synthetic polar-polymer material may comprise a mixture of different components.
  • the synthetic polar-polymer material may comprise at least one synthetic polar-component.
  • Polar in this context may mean that the component shows an enhanced polarity compared to a component that exclusively consist of C-atoms and H-atoms.
  • the synthetic polar-polymer having a Mw about > 1000 g/mol, the synthetic polar-oligomer having a Mw about > 600 g/mol and ⁇ 1000 g/mol, and the polar-additive having a Mw about > 70 and ⁇ 600 g/mol may each comprise at least about > 5 wt.-% of heteroatoms, wherein the weight % is calculated based on the individual weights of the synthetic polar-polymer, the synthetic polar-oligomer, and the polar-additive, respectively.
  • a heteroatom may be any atom excluding C-atoms and H-atoms.
  • the heteroatom may be selected from the group comprising: N, O, F, Cl, Br, I, S, and P.
  • the synthetic polar-polymer having a Mw about > 1000 g/mol, the synthetic polar-oligomer having a Mw about > 600 g/mol and ⁇ 1000 g/mol, and the polar- additive having a Mw about > 70 and ⁇ 600 g/mol may each comprise at least about > 5 wt.-% and preferably ⁇ 70 wt.-% of O-atoms.
  • the polarity of the synthetic polar-polymer material may enhance the ability of the organic aromatic dye to migrate into the synthetic polar-polymer material.
  • the synthetic polar-polymer material that is colored may comprise at least about > 0.5 wt.-% of the synthetic polar-component, preferably about > 5 wt.-% of the synthetic polar-component, and further preferred about > 10 wt.-% of the synthetic polar-component, in addition preferred about > 15 wt.-% of the synthetic polar-component, also preferred about > 20 wt.-% of the synthetic polar-component, or about > 30 wt.-% and about ⁇ 100 wt.-% of the synthetic polar-component, wherein the weight % is calculated based on the total weight of the synthetic polar-polymer material.
  • the synthetic polar-polymer material that is colored may comprise at least about > 0.5 wt.-% to about ⁇ 99.5 wt.-% of a synthetic non-polar polymer, preferably about > 5 wt.-% of the synthetic non-polar polymer, and further preferred about > 10 wt.-% of the synthetic non-polar polymer, in addition preferred about > 15 wt.-% of the synthetic non-polar polymer, also preferred about > 20 wt.-% of the synthetic non-polar polymer, or about > 30 wt.-% to about ⁇ 90 wt.-%, or about > 35 wt.-% to about ⁇ 85 wt.-%, or about > 40 wt.-% to about ⁇ 80 wt.-%, or about > 45 wt.-% to about ⁇ 75 wt.-%, or about > 50 wt.-% to about ⁇ 75 wt.-%, or about > 55 wt.-% to
  • the migration capability of the organic aromatic dye into the synthetic polar-polymer material may also be influenced by the morphology of the synthetic polar-polymer and/or the synthetic polar-oligomer. It may be possible that the synthetic polar-polymer and/or the synthetic polar-oligomer may show a mixed morphology having a mixture of crystalline phases, semi crystalline phases and amorphous phases.
  • the synthetic polar-polymer may comprise an amorphous phase of at least about > 10 vol.-%, preferably about > 30 vol.-%, more preferably about > 50 vol.-% and about ⁇ 100 vol.-%, wherein the volume % is calculated on the total volume of the synthetic polar-polymer; and/or b) the synthetic polar-oligomer may comprise an amorphous phase of at least about > 10 vol.-%, preferably about > 30 vol.-%, more preferably about > 50 vol.-% and about ⁇ 100 vol.-%, wherein the volume % is calculated on the total volume of the synthetic polar-oligomer.
  • the volume % of the amorphous phase of the synthetic polar-polymer and/or the synthetic polar-oligomer may be determined by light microscopy, light scattering, X-ray diffraction, electron microscopy, electron diffraction, and/or neutron scattering, wherein light microscopy is preferred.
  • the migration capability of the organic aromatic dye into the synthetic polar-polymer material may also be influenced by a free volume of the synthetic polar-polymer and/or the synthetic polar-oligomer. It may be advantage to the result of the dyeing process when the synthetic polar-polymer and/or the synthetic polar-oligomer trap a large amount of interconnected free volume in the glassy state.
  • the synthetic polar-polymer may have, above the glass-transition temperature T g , a free volume, in the range of about > 1 vol.-% to 25 %, preferably about > 2 % to about ⁇ 20 %, further preferred about > 2.2 % to about ⁇ 15 %, based on the total volume of the synthetic polar-polymer material; and/or
  • the synthetic polar-oligomer may have, above the glass-transition temperature T g , a free volume in the range of about > 1 % to 25 %, preferably about > 2 % to about ⁇ 20 %, further preferred about > 2.2 % to about ⁇ 15 %, based on the total volume of the synthetic polar- oligomer material.
  • the free volume may be determined by positron annihilation spectroscopy and more preferably by positron annihilation lifetime spectroscopy. These are non-destructive spectroscopy techniques for studying voids and defects in solids. The measurement data may be interpreted according to the concept of free volume given by Simha and Boyer.
  • the glass-transition temperature T g of the synthetic polar-polymer may be in the range of about > -75°C to about ⁇ 160°C, preferably about > -50°C to about ⁇ 120°C, further preferred about > 0°C to about ⁇ 115°C.
  • the glass transition may be the gradual and reversible transition in amorphous regions of the synthetic polar-polymer from a hard and relatively brittle state into a viscous or rubbery state as the temperature is increased.
  • the glass transition temperature T g of the synthetic polar- polymer may be determined by differential scanning calorimetry (DSC), which is a
  • thermoanalytical technique in which the difference in the amount of heat required to increase the temperature of a sample and reference is measured as a function of temperature.
  • the glass transition temperature T g of the synthetic polar-polymer may be determined according to the following standards: DIN 51007 (Thermal Analysis - Differential Thermal Analysis and Differential Scanning Calorimetry - General Principles), ASTM E 474, ASTM D 3418, DIN EN ISO 11357-1 (Plastics - Differential Scanning Thermal Analysis Part 1 : General principles. (2008)), ISO 11357-2 (Plastics - Differential Scanning Calorimetry Part 2:
  • the glass transition temperature T g of the synthetic polar-polymer may be determined using a Mettler Toledo DSC 3+ differential calorimeter, a sample amount of 10 +/- 1 mg, nitrogen as purge gas, and the following settings: 1.
  • the synthetic polar-polymer may be selected from the group comprising synthetic polar- homopolymers, synthetic polar-copolymers, and/or synthetic polar-terpolymers; and/or b) the synthetic polar-oligomer may be selected from the group comprising synthetic polar-homo oligomers, synthetic polar-cooligomers, and/or synthetic polar-teroligomers.
  • a homopolymer or a homo oligomer may be a polymer or an oligomer that contains only a single type of repeat unit.
  • a copolymer or a cooligomer may be a polymer or an oligomer that contains two types of repeat units.
  • a terpolymer or a teroligomer may be a polymer or an oligomer that contains three types of repeat units.
  • the different types of repeat units may be organized along the backbone in different ways. There may be a controlled arrangement of the different repeat units, a statistical distribution of the different repeat units, and/or a longer sequence of one specific repeat unit alternating a longer sequence of a different specific repeat unit.
  • the two different types of repeat units in the copolymer or the cooligomer are organized in blocks such that the copolymer or the cooligomer is a block copolymer or block cooligomer.
  • the first type of repeat unit is non-polar and preferably comprises only C and H atoms.
  • the second type of repeat unit is polar and comprises more than 5 wt.-% of heteroatoms based on the total weight of the repeat unit, wherein a heteroatom is any atom excluding C and H.
  • These block copolymers and block oligomers may have the advantage that the migration of the organic aromatic dye into the synthetic polar-polymer material is enhanced due to the formation of micelles and kind of channels in the synthetic polar-polymer material.
  • block copolymers and/or block cooligomers may lead to a more homogenous dyeing of the synthetic polar-polymer material.
  • These block copolymers and block oligomers may be produced by (living) radical polymerization and or radical oligomerization and/or by using coordinative polymerization methods with metal complex catalysts.
  • Synthetic polar-polymer or mixture The synthetic polar-polymer or mixture thereof may be selected from the group comprising:
  • (meth)acrylate pentyl(meth)acrylate and 2-ethylhexyl(meth)acrylate;
  • (Meth)acrylates derived from unsaturated alcohols preferably oleyl(meth)acrylate, 2-propynyl(meth)acrylate, allyl(meth)acrylate, vinyl(meth)acrylate;
  • - aryl(meth)acrylates polymers preferably benzyl(meth)acrylate polymers or
  • phenyl(meth)acrylate polymers the aryl radicals each being unsubstituted or up to four times substituted;
  • - cycloalkyl(meth)acrylates polymers preferably 3-vinylcyclohexyl(meth)acrylate polymers, bornyl (meth)acrylate polymers;
  • - hydroxylalkyl (meth)acrylates polymers preferably 3- hydroxypropyl (meth)acrylate polymers, 3,4- dihydroxybutyl(meth)acrylate polymers, 2-hydroxy ethyl(meth)acrylate polymers, 2- hydroxypropyl(meth)acrylate polymers;
  • glycol di(meth)acrylates polymers preferably 1,4-butanediol (meth)acrylate polymers
  • - (meth)acrylates of ether alcohols polymers preferably tetrahydrofurfuryl (meth)acrylate polymers, vinyloxyethoxyethyl(meth)acrylate polymers;
  • - vinyl ester polymers preferably vinyl acetate polymers
  • - styrene polymers substituted styrene polymers with an alkyl substituent in the side chain, preferably a-methylstyrene and a-ethylstyrene, substituted styrene polymers with an alkyl substituent on the ring, preferably vinyl toluene, and ⁇ -methylstyrene, halogenated styrene polymers, preferably monochlorostyrene polymers, dichlorostyrene polymers, tribromostyrene polymers and tetrabromostyrene polymers;
  • - heterocyclic vinyl polymers preferably 2-vinylpyridine polymers, 3-vinylpyridine polymers, 2- methyl-5-vinylpyridine polymers, 3-ethyl-4-vinylpyridine polymers, 2,3-dimethyl-5- vinylpyridine polymers, vinylpyrimidine polymers, vinylpiperidine polymers, 9-vinylcarbazole polymers, 3 -vinylcarbazole polymers, 4-vinylcarbazole polymers, 1 -vinylimidazole polymers, 2-methyl- 1 -vinylimidazole polymers, N-vinylpyrrolidone polymers, 2-vinylpyrrolidone polymers, N-vinylpyrrolidine polymers, 3-vinylpyrrolidine polymers, N-vinylcaprolactam polymers, N-vinylbutyrolactam polymers, vinyl oxolane polymers, vinyl furan polymers, vinyl thiophene polymers, vinylthiolane polymers, vinylthiazo
  • maleic acid polymers preferably maleic anhydride polymers, methyl maleic anhydride polymers, maleimide polymers, methyl maleimide;
  • polyesters preferabyl, hydroxyl-functional dendritic polyesters, polycaprolactone, polyethylenterephthalate (PET), polytrimethylenterephthalat (PTT), polybutylenterephthalat (PBT), glycolized polyglycolterephthaltat (G-PET), amorphous polyethylenterephthalat (A-PET), polyesters of terephthalic acid, polyspiro-diol-terephthalate, polypentaspiroglycol-terephthalate (PSG), polycyclohexylenedimethylene-terephthalate (PCT), polyester based copolymer including a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid and a diol-derived residue including a residue derived from 4-(hydroxymethyl)cyclohexylmethyl-4’ -(hydroxymethyl)cyclohexane carboxylate, polyester based copo
  • PC polycarbonate
  • 2,2-Bis-(4-hydroxyphenyl)-propan Bisphenol A
  • 2,2-Bis- (4-hydroxyphenyl)-butan Bisphenol B) polycarbonate
  • l,l-Bis(4-hydroxyphenyl)cyclohexan Bisphenol C
  • 2,2’-Methylendiphenol Bisphenol F
  • bisphenol S polycarbonate dihydroxydiphenylsulfid polycarbonate
  • tetramethylbisphenol A polycarbonate l,l-Bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (BPTMC) polycarbonate
  • l,l,l-Trimethylcyclohexane BPTMC
  • PA - aliphatic polyamide
  • PA 6 based on poly caprolactam
  • PA 6.6 based on 6,6- hexamethylendiamin and adipic acid
  • PA 6.66 based on caprolactam
  • PA 66.610 based on hexamethylendiamin, copolymer of adipic acid and sebaic acid, PA 4.6, PA10, PA 12 and PA copolymers;
  • - polar-terpolymere preferably reactive terpolymers of ethylene, acrylic ester and maleic anhydride, or ethylene, methacrylic ester and maleic anhydride, or ethylene, acrylic esters and glycidyl methacrylate, or ethylene, methacrylic esters and glycidyl methacrylate, or ethylene, (meth)acrylic esters and methyl (methyl(meth)acrylate), ethyl (ethy(meth)acrylate), propyl (propyl(meth)acrylate), or butyl (butyl(meth)acrylate), polyamide, polyester-polyamides, or butyl (butyl(meth)acrylate), polyether-polyamide copolymers;
  • PC/PET blends polycarbonate/polyethylenterephthalat blends
  • PC/PBT blends polycarbonate/polybutyleneterephthalate blends
  • blends of polycyclohexylene dimethylene terephthalate copolymer blends of poly(butylene-adipate- terephthalate);
  • ABS acrylonitrile butadiene styrene
  • polystyrene and polystyrene copolymers preferably styrene/butadiene co-polymer (SBR), poly styrene-isoprene-styrene (SIS), poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine;
  • SBR styrene/butadiene co-polymer
  • SIS poly styrene-isoprene-styrene
  • polyether preferably polyethyleneglycol, polyethyleneglycol with at least one fatty acid coupled to the polyethyleneglycol, terminating functional groups such NEb-terminated poly ethers;
  • polyacrylamide polymers, copolymers and terpolymers preferably poly(2- acrylamido-2-aminopropionicacid) (poly AMP A), poly(2-acrylamido-2-amino propane sulfonic acid), poly(N-isopropylacylamide (polyPNIPAM); poly (amidoamine-co-acrylic acid) copolymer, poly(N,N-dimethylacrylamide-co-sodium acrylate), poly(acrylamide-co-sodium acrylate)/poly(ethylene glycol) semi-IPN, poly(acrylamide-co-sodium 4-styrenesulfonate), poly(acrylamide-co-sodium 4-styrenesulfonate)/poly(ethylene glycol) semi-IPN,
  • methacrylate /poly(ethylene glycol) semi-IPN, and/or poly(N-isopropylacrylamide-co-acrylic acid) andpoly(acrylamide-co-acrylic acid;
  • polyvinylpyrrolidone preferably poly(N-vinyl-2-pyrrolidone), poly(N-vinyl-2-pyrrolidone-co- acrylonitrile) treated with hydroxylamine-hydrochloride
  • hydroxyl-functional dendritic polyesters that can be suitable used as a polar polymers
  • these molecules may be produced using polyalcohol cores, hydroxy acids and technology based on captive materials.
  • the dendritic structures may be formed by polymerization of the particular core and 2,2-dimethylol propionic acid (Bis-MPA).
  • the base products that may be obtained are hydroxyl-functional dendritic polyesters. They may be fully aliphatic and may consist only of tertiary ester bonds. They may provide excellent thermal and chemical resistance. Extensive branching also improves reactivity, lowers viscosity and results in balanced mechanical properties.
  • the hydroxyl-functional dendritic polyesters may be known under the trade name Boltorn®.
  • the following dendritic polymers may be used as non-limiting examples: Boltorn® H20 16 terminal hydroxyl groups, nominal molecular weight of 1750 g/mol, Boltorn® H2004 6 terminal hydroxyl groups, nominal molecular weight of 3100 g/mol, Boltorn® H311 23 terminal hydroxyl groups, nominal molecular weight of 5300 g/mol, Boltorn® P500 Formulated bimodal product with terminal hydroxyl groups, nominal molecular weight 1800 g/mol, Boltorn® PI 000 formulated bimodal product with terminal hydroxyl groups, nominal molecular weight 1500 g/mol, Boltorn® U3000 modified with unsaturated fatty acid, nominal molecular weight 6500 g/mol, Boltorn® W3000 modified with non-ionic groups and unsaturated fatty acid, nominal molecular weight 10000 g/mol.
  • polyester based copolymers that can be suitable used as a polar polymers, these may further include but not limited to a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid and a diol-derived residue including a residue derived from 4-(hydroxymethyl)cyclohexylmethyl-4’- (hydroxymethyl)cyclohexane carboxylate represented by the following chemical formula 1 and a residue derived from 4,4-(oxybis(methylene)bis) cyclohexane methanol represented by the following chemical formula 2.
  • the compounds of chemical formula 1 and 2 can be copolymerized with aromatic dicarboxylic acid may be one or more selected from a group consisting of terephthalic acid, dimethyl terephthalate, cyclic dicarboxylic acid, isophthalic acid, adipic acid, azelaic acid, naphthalene dicarboxylic acid, and succinic acid.
  • the diol-derived residue of the copolymers may further include a residue derived from one or more other diols selected from a group consisting of 1,4-cyclohexane dimethanol, 1,2- propanediol, 1,3-propanediol, 1,4-butanediol, 2, 2-dimethyl- 1,3-propanediol, 1,6-hexanediol, 1,2- cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexane dimethanol, 1,3-cyclohexane dimethanol, 2,2-dimethylpropane-l,3-diol (neopentyl glycol), ethylene glycol, and diethylene glycol.
  • 1,4-cyclohexane dimethanol 1,2- propanediol, 1,3-propanediol, 1,4-butanediol, 2, 2-dimethyl- 1,3-propaned
  • a content of the diol derived residues of the residue derived from 4-(hydroxymethyl)cyclohexyl- methyl 4’-(hydroxymethyl)cyclohexane carboxylate, the residue derived from 4,4- (oxybis(methylene)bis) cyclohexane methanol, and other diol-derived residues may be about 10 to 80 mol% based on 100 mol% of the dicarboxylic acid co-monomer.
  • the synthetic polar-polymer may also comprise the polyester based copolymers used in a mixture with polyethylene terephthalate (PET).
  • the mixture may consist of 1 to 99 wt.-% of PET and 1 to 99 wt.-% of the polyester based copolymers, in order that both components add up to 100 wt.-%.
  • the compounds according to chemical formulas 1 and 2 may be used as co-monomers together with a further diol-component, e.g. ethylene glycol, in the preparation of the polyester based copolymers.
  • the polyester based copolymer may be prepared by reacting the dicarboxylic acid including the aromatic dicarboxylic acid with the diol including 4-(hydroxymethyl)cyclohexyl- methyl 4’-(hydroxymethyl)cyclohexane carboxylate represented by chemical formula 1 and 4,4- (oxybis(methylene)bis) cyclohexane methanol represented by chemical formula 2 to perform an esterification reaction and a polycondensation reaction.
  • other diols such as 1,4- cyclohexane dimethanol, ethylene glycol, diethylene glycol, or the like, as described above may be further reacted, such that a polyester based copolymer further including other diol-derived residues may be prepared.
  • poly ether may comprise but not limited to compounds that contain at least one polyethyleneglycol moiety and at least one fatty acid moiety coupled to the poly ethyleneglycol moiety.
  • the poly ethyleneglycol moiety may contain 10 to 25 ethyleneglycol repeating units.
  • the fatty acid moieties may be saturated or unsaturated and may contain 10 to 30 carbon atoms, preferably 16 to 22 carbon atoms. Examples of these fatty acid moieties are oleate, laureate, stearate, palmitate and ricinoleate. A specific preferred example may be ethoxylated sorbitan ester.
  • the ethoxylated sorbitan ester comprises a sorbitan group which is substituted by four polyethylene glycol substituents.
  • the ethoxylated sorbitan ester may preferably comprise 14 to 26 ethylene glycol repeating units, preferably 16 to 24 ethylene glycol repeating units, more preferably between 18 and 22 repeating units. At least one of the ethylene glycol substituents in the ethoxylated sorbitan ester is connected via an ester bond to a fatty acid moiety.
  • At least two of the ethylene glycol substituents in the ethoxylated sorbitan ester are connected via an ester bond to a fatty acid moiety; more preferably at least three of the ethylene glycol substituents are connected via an ester bond to a fatty acid moiety.
  • the fatty acid moieties may be saturated or unsaturated and may contain 10 to 30 carbon atoms, preferably 16 to 22 carbon atoms.
  • fatty acid moieties examples are oleate, laureate, stearate and palmitate.
  • ethoxylated sorbitan esters comprising four polyethylene glycol substituents and wherein the ester comprises between 18 and 22 ethylene glycol repeating units and wherein three of the ethylene glycol substituents are connected to oleate, laurate or stearate groups.
  • ethoxylated sorbitan esters that can be used as polar-polymer are polyoxyethylene (20) sorbitane monolaurate, polyoxyethylene (20) sorbitane dilaurate, polyoxyethylene (20) sorbitane trilaurate, polyoxyethylene (20) sorbitane mono-oleate, polyoxyethylene (20) sorbitane di-oleate, polyoxyethylene (20) sorbitane tri-oleate,
  • polyoxyethylene (20) sorbitane monostearate, polyoxyethylene (20) sorbitane distearate, polyoxyethylene (20) sorbitane tristearate, and polyoxyethylene (20) sorbitan monooleate also known as Polysorbate 80 and E433.
  • - oligomethacrylate with methyl oligomethylmathacrylate
  • ethyl oligoethylmethacrylate
  • propyl oligopropylmethacrylate
  • butyl oligobutylmethacrylate
  • (meth)acrylate pentyl(meth)acrylate and 2-ethylhexyl(meth)acrylate;
  • (Meth)acrylates derived from unsaturated alcohols preferably oleyl(meth)acrylate, 2-propynyl(meth)acrylate, allyl(meth)acrylate, vinyl(meth)acrylate;
  • - aryl(meth)acrylates oligomers preferably benzyl(meth)acrylate oligomers or
  • phenyl(meth)acrylate oligomers the aryl radicals each being unsubstituted or up to four times substituted;
  • - cycloalkyl(meth)acrylates oligomers preferably 3-vinylcyclohexyl(meth)acrylate oligomers, bornyl (meth)acrylate oligomers;
  • - hydroxylalkyl (meth)acrylates oligomers preferably 3- hydroxypropyl (meth)acrylate oligomers, 3,4- dihydroxybutyl(meth)acrylate oligomers, 2-hydroxyethyl(meth)acrylate oligomers, 2-hydroxypropyl(meth)acrylate oligomers;
  • - glycol di(meth)acrylates oligomers preferably 1,4-butanediol (meth)acrylate oligomers
  • - (meth)acrylates of ether alcohols oligomers preferably tetrahydrofurfuryl (meth)acrylate oligomers, vinyloxyethoxyethyl(meth)acrylate oligomers;
  • - oligomers of amides and nitriles of the (meth)acrylic acid preferably N-(3- dimethylaminopropyl)(meth)acrylamide oligomers, N-(diethylphosphono)(meth)acrylamide oligomers, 1 -methacryloylamido-2-methy 1-2-propanol oligomers;
  • oligomers of sulfur-containing methacrylates preferably ethylsulfinylethyl( meth)acrylate, 4- thiocyanatobutyl(meth)acrylate oligomers, ethylsulfonylethyl(meth)acrylate oligomers, thiocyanatomethyl(meth)acrylate oligomers, methylsulfinylmethyl(meth)acrylate oligomers, bis((meth)acryloyloxyethyl)sulfide oligomers;
  • oligohydric (meth)acrylates preferably trimethyloylpropanetri(meth)acrylate oligomers
  • styrene oligomers substituted styrenes oligomers with an alkyl substituent in the side chain, preferably a-methylstyrene and a -ethylstyrene, substituted styrenes oligomers with an alkyl substituent on the ring, preferably vinyl toluene, and p-methylstyrene, halogenated styrene oligomers, preferably monochlorostyrene oligomers, dichlorostyrene oligomers,
  • - heterocyclic vinyl oligomers preferably 2-vinylpyridine oligomers, 3-vinylpyridine oligomers, 2-methyl-5-vinylpyridine oligomers, 3-ethyl-4-vinylpyridine oligomers, 2,3-dimethyl-5- vinylpyridine oligomers, vinylpyrimidine oligomers, vinylpiperidine oligomers, 9- vinylcarbazole oligomers, 3-vinylcarbazole oligomers, 4-vinylcarbazole oligomers, 1- vinylimidazole oligomers, 2-methyl- 1 -vinylimidazole oligomers, N-vinylpyrrolidone oligomers, 2-vinylpyrrolidone oligomers, N-vinylpyrrobdine oligomers, 3-vinylpyrrolidine oligomers, N- vinylcaprolactam oligomers, N-vinylbutyrolactam oligomers, vinyl oxolane
  • maleic acid oligomers preferably maleic anhydride oligomers, methyl maleic anhydride oligomers, maleimide oligomers, methyl maleimide;
  • oligoesters preferably oligocaprolactone, oligoethylenterephthalate (PET), oligotrimethylenterephthalat (PTT), obgobutylenterephthalat (PBT), glycolized oligoglycolterephthaltat (G-PET), amorphes oligoethylenterephthalat (A-PET), oligoesters of terephthalic acid, oligospiro-diol-terephthalate, oligopentaspiroglycol-terephthalate (PSG), polycyclohexylenedimethylene-terephthalate, oligoester based cooligomer including a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid and a diol-derived residue including a residue derived from 4-
  • digester based cooligomer including a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid and a diol-derived residue including a residue derived from 4,4- (oxybis(methylene)bis) cyclohexane methanol;
  • oligocarbonate (PC), 2,2-Bis-(4-hydroxyphenyl)-propan (Bisphenol A) oligocarbonate, 2,2- Bis-(4-hydroxyphenyl)-butan (Bisphenol B) oligocarbonate, l,l-Bis(4- hydroxyphenyl)cyclohexan (Bisphenol C) oligocarbonate, 2,2’ -Methylendi phenol (Bisphenol F) oligocarbonate, 2,2-Bis(3,5-dibrom-4-hydroxyphenyl)propan (Tetrabrombisphenol A) oligocarbonate und 2,2-Bis(3,5-dimethyl-4-hydroxyphenyl)propan (Tetramethylbisphenol A) oligocarbonate, bisphenol S oligocarbonate, dihydroxydiphenylsulfid oligocarbonate, tetramethylbisphenol A oligocarbonate, l,l-Bis(4-hydroxyphenyl)-3,3,5-
  • PA - aliphatic oligoamide
  • PA 6 based on oligocapro lactam
  • PA 6.6 based on 6,6- hexamethylendiamin and adipic acid
  • PA 6.66 based on caprolactam
  • PA 66.610 based on hexamethylenediamine, cooligomer of adipic acid and sebaic acid, PA 4.6, PA10, PA 12 and PA cooligomers;
  • - polar-teroligomere preferably reactive teroligomers of ethylene, acrylic ester and maleic anhydride, or ethylene, methacrylic ester and maleic anhydride, or ethylene, acrylic esters and glycidyl methacrylate, or ethylene, methacrylic esters and glycidyl methacrylate, or ethylene, (meth)acrylic esters and methyl (methyl(meth)acrylate), ethyl (ethy(meth)acrylate), propyl (propyl(meth)acrylate), or butyl (butyl(meth)acrylate), oligoamide, oligoester-oligoamides, or butyl (butyl(meth)acrylate), oligoether-oligoamide cooligomers;
  • oligocarbonate/oligoethylenterephthalat blends PC/PET blends
  • oligocarbonate/oligobutyleneterephthalate blends PC/PBT blends
  • blends of oligocyclohexylene dimethylene terephthalate cooligomer blends of oligo(butylene-adipate- terephthalate);
  • oligoacrylnitril and oligoacrylnitril-cooligomers preferably oligo acrylonitrile butadiene styrene (ABS), oligo styrene-acrylonitrile;
  • oligostyrene and oligostyrene cooligomers preferably styrene/butadiene co-oligomer (SBR), oligo styrene-isoprene-styrene (SIS), oligo(glycidyl methacrylate) grafted sulfonamide based oligostyrene resin with tertiary amine;
  • oligoether preferably obgoethyleneglycol, oligoethyleneglycol with at least one fatty acid coupled to the obgoethyleneglycol, oligoether with terminating functional groups, preferbyl NEh-terminated obgoethers,
  • oligoacrylamide oligomers preferably obgo(2- acrylamido-2-aminopropionicacid) (oligoAMPA), oligo(2-acrylamido-2-amino propane sulfonic acid), oligo(N-isopropylacylamide (obgoPNIPAM); oligo (amidoamine-co-acrylic acid) co-oligomer, oligo(N,N-dimethylacrylamide-co-sodium acrylate), oligo(acrylamide-co- sodium acrylate)/obgo(ethylene glycol) semi-IPN, oligo(acrylamide-co-sodium 4- styrenesulfonate), oligo(acrylamide-co-sodium 4-styrenesulfonate)/oligo(ethylene glycol) semi- IPN, oligo(acrylamide-co-sodium methacrylate), oligo(acrylamide-co
  • oligovinylpyrrobdone preferably obgo(N-vinyl-2-pyrrolidone), obgo(N-vinyl-2-pyrrolidone- co-acrylonitrile) treated with hydroxylamine-hydrochloride
  • oligoester based cooligomers that can be suitable used as a polar oligomers, these may further include but not limited to a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid and a diol-derived residue including a residue derived from 4-(hydroxymethyl)cyclohexylmethyl-4’- (hydroxymethyl)cyclohexane carboxylate represented by the following chemical formula 1 and a residue derived from 4,4-(oxybis(methylene)bis) cyclohexane methanol represented by the following chemical formula 2.
  • a dicarboxylic acid-derived residue including a residue derived from an aromatic dicarboxylic acid
  • a diol-derived residue including a residue derived from 4-(hydroxymethyl)cyclohexylmethyl-4’- (hydroxymethyl)cyclohexane carboxylate represented by the following chemical formula 1
  • the compounds of chemical formula 1 and 2 can be cooligomerized with aromatic dicarboxylic acid may be one or more selected from a group consisting of terephthalic acid, dimethyl terephthalate, cyclic dicarboxylic acid, isophthalic acid, adipic acid, azelaic acid, naphthalene dicarboxylic acid, and succinic acid.
  • the diol-derived residue of the cooligomers may further include a residue derived from one or more other diols selected from a group consisting of 1,4-cyclohexane dimethanol, 1,2- propanediol, 1,3-propanediol, 1,4-butanediol, 2, 2-dimethyl- 1,3-propanediol, 1,6-hexanediol, 1,2- cyclohexanediol, 1,4-cyclohexanediol, 1,2-cyclohexane dimethanol, 1,3-cyclohexane dimethanol, 2,2-dimethylpropane-l,3-diol (neopentyl glycol), ethylene glycol, and diethylene glycol.
  • 1,4-cyclohexane dimethanol 1,2- propanediol, 1,3-propanediol, 1,4-butanediol, 2, 2-dimethyl- 1,3-propaned
  • a content of the diol derived residues of the residue derived from 4-(hydroxymethyl)cyclohexyl- methyl 4’-(hydroxymethyl)cyclohexane carboxylate, the residue derived from 4,4- (oxybis(methylene)bis) cyclohexane methanol, and other diol-derived residues may be about 10 to 80 mol% based on 100 mol% of the dicarboxylic acid co-monomer.
  • the synthetic polar-oligomer may also comprise the oligoester based cooligomers used in a mixture with oligoethylene terephthalate (PET).
  • PET oligoethylene terephthalate
  • the mixture may consist of 1 to 99 wt.-% of PET and 1 to 99 wt.-% of the oligoester based cooligomers, in order that both components add up to 100 wt.-%.
  • the compounds according to chemical formulas 1 and 2 may be used as co-monomers together with a further diol-component, e.g. ethylene glycol, in the preparation of the oligoester based cooligomers.
  • the oligoester based cooligomer may be prepared by reacting the dicarboxylic acid including the aromatic dicarboxylic acid with the diol including 4-(hydroxymethyl)cyclohexyl- methyl 4’-(hydroxymethyl)cyclohexane carboxylate represented by chemical formula 1 and 4,4- (oxybis(methylene)bis) cyclohexane methanol represented by chemical formula 2 to perform an esterification reaction and a oligocondensation reaction.
  • oligoether may comprise but not limited to compounds that contains at least one oligoethyleneglycol moiety and at least one fatty acid moiety coupled to the oligoethyleneglycol moiety.
  • the oligoethyleneglycol moiety may contain 8 or 9 ethyleneglycol repeating units.
  • the fatty acid moieties may be saturated or unsaturated and may contain 10 to 30 carbon atoms, preferably 16 to 22 carbon atoms.
  • Examples of these fatty acid moieties are oleate, laureate, stearate, palmitate and ricinoleate.
  • Examples of compound that contain at least one polyethyleneglycol moiety and at least one fatty acid moiety coupled to the poly ethyleneglycol moiety include PEG 300 di-oleate, PEG 300-distearate, PEG 400 dioleate, PEG 400 distearate, PEG 400 monooleate, PEG 400 monoricinoleate, PEG 400 monostearate.
  • a specific preferred example may be ethoxylated sorbitan oligoester.
  • the ethoxylated sorbitan oligoester comprises a sorbitan group which is substituted by four oligoethylene glycol substituents.
  • the ethoxylated sorbitan ester may preferably comprise 14 to 26 ethylene glycol repeating units, preferably 16 to 24 ethylene glycol repeating units, more preferably between 18 and 22 repeating units. At least one of the ethylene glycol substituents in the ethoxylated sorbitan ester is connected via an ester bond to a fatty acid moiety.
  • At least two of the ethylene glycol substituents in the ethoxylated sorbitan ester are connected via an ester bond to a fatty acid moiety; more preferably at least three of the ethylene glycol substituents are connected via an ester bond to a fatty acid moiety.
  • the fatty acid moieties may be saturated or unsaturated and may contain 10 to 30 carbon atoms, preferably 16 to 22 carbon atoms.
  • fatty acid moieties examples are oleate, laureate, stearate and palmitate.
  • ethoxylated sorbitan esters comprising four oligoethylene glycol substituents and wherein the ester comprises between 18 and 22 ethylene glycol repeating units and wherein three of the ethylene glycol substituents are connected to oleate, laurate or stearate groups.
  • the polar additive may be solid at 23 °C.
  • the polar additive may not be a dye.
  • the polar additive may be solid at 23 °C and is not a dye.
  • the polar additive may be solid at 23 °C and is not a dye, is selected different from the dispersing agent and is selected different from the solubilizer.
  • the polar- additive having a Mw about > 70 and ⁇ 600 g/mol may be selected from the group comprising aliphatic acids CH3-[CH2] n -COOH acids (n about > 3), amino acids, carboxylic acid amide, hydroxyl acids, fatty acids, aliphatic or aliphatic/aromatic aldehydes and ketones, esters, pentaerythritol, pentaerythritol dimers, pentaerythritol trimers, pentaerythritol ester preferably carboxylic acid ester, benzoic acid esters comprising benzylbenzoat or phenylbenzoat, phenylether, alcohols and polyvalent alcohols, preferably glycerine, amines, wherein the polar- additive is selected different to the organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about
  • the carboxylic acid amide may comprise a compound according to formula
  • Pentaerythritol may comprise a compound according to formula C(CH 2 0R) 4 , wherein R may be H, or wherein R may be a fatty acid moiety comprising 5-8 carbon atoms.
  • the fatty acid moieties can be saturated or unsaturated.
  • R may be also another moiety like ether, amide and/or urethane.
  • Pentaerythritol Perstorp Charmor PM 40 may be used.
  • the polar additive may be an ether.
  • Ether these may comprise but not limited to compounds that contains at least one ethyleneglycol moiety and at least one fatty acid moiety coupled to the ethyleneglycol moiety.
  • Examples of compound that contains at least one ethyleneglycol moiety and at least one fatty acid moiety coupled to the poly ethyleneglycol moiety include PEG 300-monostearate, PEG 400 monolaurate.
  • the carboxylic acid ester may comprise a compound according to the following chemical formula 3 : wherein R 1 is an alkyl group comprising 1 -20 carbon atoms and Z is hydrogen or a group according to the formula C(0)R 2 , wherein R 2 is an alkyl group comprising 1-20 carbon atoms.
  • R 1 may be the same or different and is an alkyl group comprising 1-20 carbon atoms, preferably 1- 15 carbon atoms, more preferably 1-10 carbon atoms.
  • R 2 is an alkyl group comprising 1-20 carbon atoms, preferably 1-10 carbon atoms, more preferably 1-5 carbon atoms.
  • the synthetic polar-polymer material that is colored may comprise a composition of a non-polar-polymer having a Mw about > 1000 g/mol.
  • the non-polar-polymer may be selected from the group of polyalkylene polymers, polyalkylene copolymers, polyakylene block copolymers.
  • the non-polar-polymer may be preferably selected from of polymeric aliphatic or aromatic hydrocarbons, preferably
  • polyalkylene polymers polyalkylene co- and terpolymer with random or block-structure; and more preferred from polyethylen (PE), polypropylene (PP), polybutene (PB), polystyrene, poly isobutylene, poly butadiene, polyisoprene.
  • PE polyethylen
  • PP polypropylene
  • PB polybutene
  • polystyrene poly isobutylene
  • poly butadiene polyisoprene
  • the non-polar-polymer may have a wt- % of heteroatoms below 5 wt.-% with respect to the mass of the non-polar-polymer.
  • the organic aromatic dye is not a chemical reactive dye. That means the organic aromatic dye as used in the present invention doesn’t covalently bond to a component of the polymer material that is colorized by the organic aromatic dye. In this context forming no chemical covalent bond means that the organic aromatic dye does not form a covalent sigma bond, covalent double bound, covalent triple bond or any other chemical covalent bond with the synthetic polar-polymer material or with a component of the synthetic polar polymer material.
  • the organic aromatic dye for example adsorbs and/or absorbs to the polar-polymer component. It has not been examined if the organic aromatic dye for example adsorbs and/or absorbs to the polar-polymer component. It seems more likely that the organic aromatic dye adsorbs to the polar-polymer component.
  • the organic aromatic dye may have a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol, preferably the organic aromatic dye has a molecular weight Mw in the range of about > 270 g/mol to about ⁇ 450 g/mol, and more preferably the organic aromatic dye has a molecular weight Mw in the range of about > 285 g/mol to about ⁇ 400 g/mol.
  • the organic aromatic dye may absorb light in the visible spectrum; therefore it may appear to be colored for a human observer. Furthermore it may also be possible that the organic aromatic dye absorbs light in the UV or in the infrared region of the electromagnetic spectrum. In this case the organic aromatic dye may not appear to have a visible color to a human observer. It may also be possible that the organic aromatic dye is a stabilizer to prevent the oxidation, chain fission, uncontrolled recombination and/or cross-linking reaction that are caused by photo oxidation of the synthetic polar polymer material.
  • the synthetic polar polymer material may become weathered by the direct or indirect impact of heat and ultraviolet light. This effect may be hindered by hindered amine light stabilizers (HALS).
  • HALS hindered amine light stabilizers
  • the solubility of the organic aromatic dye in water may be low.
  • the organic aromatic dye may have a solubility in water at 23 °C of about ⁇ 0.1 g/1 and > 0 g/1, preferably about ⁇ 0.01 g/1 and > 0 g/1, more preferably about ⁇ 0.001 g/1 and > 0 g/1.
  • the organic aromatic dye may comprise at least 2 to 6 aromatic six-membered rings, or at least 3 to 5 aromatic six-membered rings and at least 1 to 4 five-membered rings.
  • the aromatic dye may have at least 2 to 6 aromatic six-membered rings and/or the organic aromatic dye may comprises at least on heteroatom selected from N, O, S, Br.
  • the organic aromatic dye is selected from the group comprising the following chemical formulas A1 to A10 according to table 1 :
  • the methoxy group -[OCH 3 ] may be an alternative for the hydroxyl group -[OH] on the aromatic moiety, that is not part of the anthraquinone ring system.
  • organic aromatic dye may be selected from the group comprising Bis(2, 2,6,6- tetramethyl-4-piperidyl)sebacat, methyl l,2,2,6,6-pentamethyl-4-piperidyl sebacate, 2,2'- Thiobis(4-tert-octylphenolato)-n-butylamine nickel(II), N-(2-Ethoxyphenyl)-N'-(4-ethylphenyl)- ethlyene diamide.
  • the organic aromatic dye may include UV-absorbers form the company European Additives GmbH and the light stabilizers from the company MPI Chemie B.V.
  • the organic aromatic dye is selected from the group comprising the dyes known under the trademark BEMACRON S/SE/E from CHT Germany GmbH, or from Dystar Pte Ltd.
  • the organic aromatic dye is selected from the group comprising BEMACRON Yellow S-6GF, BEMACRON Yellow S-4g, BEMACRON Yellow Brown S-2RF1, BEMACRON Orange S-g, BEMACRON Scarlet S-gFl, BEMACRON Scarlet S-BWF1, BEMACRON Rubine S-2GFL, BEMACRON Violet S-3R1, BEMACRON Violet S-B1F, BEMACRON Blue S-Bgl, BEMACRON Blue S-BB, BEMACRON Turquoise S-gF, BEMACRON Navy S-2gl,
  • BEMACRON Black SE-R1X BEMACRON Black SE-Rd2R, BEMACRON Yellow E-3gl, BEMACRON Red E-FBI, BEMACRON Blue E-FBI, and BEMACRON Black E-R.
  • organic aromatic dye is selected from the group comprising
  • BEMACRON Black E-R BEMACRON Yellow S-6GF, BEMACRON Rubine S-2GFL, BEMACRON Blue RS, BEMACRON Blue E-FBL 150, BEMACRON Red E-FBL,
  • the aromatic dye may not comprise a phthalocyanine.
  • the dispersing agent may be selected from the group comprising at least one:
  • anionic tenside preferably selected from polyphosphates, polyacrylates, aromatic sulfonates, esters with ethoxylate groups, esters with sulfonate groups, fatty acid-based polymers with an anionic group, salts of polycarboxylic acids, ethoxylates, thiourea dioxide;
  • - cationic tenside preferably selected from quaternary ammonium compounds, fatty acid- polymers with a cationic group per molecule;
  • - non-ionic tenside preferably selected from aromatic esters and hydrocarbons, aromatic and non-aromatic carboxylic acid esters, ethyl acrylate, fatty acid esters, ethoxylated fatty acid, polymers that are fatty acid-based with a non-ionic group per molecule, acrylate-copolymers, acrylate/styrene copolymers, fatty acid derivatives, polyalkoxylate;
  • PUR polyurethane
  • PUR polyurethane
  • the polyacrylate polymers may be preferably selected from the Efka® 4000 series from BASF SE.
  • the dispersing agent may contain tertiary nitrogen compounds.
  • a dispersing agent that can be suitable used may be a substance that holds two or more immiscible liquids or solids in suspension, e.g., water and the organic aromatic dye.
  • Dispersing agents which may be used include ionic dispersing agent, non-ionic dispersing agent, or mixtures thereof.
  • Typical ionic dispersing agents are anionic dispersing agents, including amine salts or alkali salts of carboxylic, sulfamic or phosphoric acids, for example, sodium lauryl sulfate, ammonium lauryl sulfate, lignosulfonic acid salts, ethylene diamine tetra acetic acid (EDTA) sodium salts and acid salts of amines such as laurylamine hydrochloride or poly(oxy-l,2 ethanediylphenyl)alpha-sulfo-omega-hydroxy ether with phenol 1 -(methylphenyl)ethyl derivative ammonium salts; or amphoteric, that is, compounds bearing both anionic and cationic groups, for example, lauryl sulfobetaine; dihydroxy ethylalkyl betaine; amido betaine based on coconut acids; disodium N-lauryl amino propionate; or the sodium salts of dicarbox
  • Typical non-ionic dispersing agents include but not limited to ethoxylated or propoxylated alkyl or aryl phenolic compounds, such as, octylphenoxypolyethyleneoxyEthanol or poly(oxy-l,2-ethanediyl)alpha-phenyl-omega-hydroxy, styrenated.
  • An another dispersing agent may be a mixture of C14-C18 and C16-C18 ethoxylated unsaturated fatty acids and poly(oxy-l,2- ethanediyl)alpha-sulfo-omega-hydroxy ether with phenol l-(methylphenyl)ethyl derivative ammonium salts and poly(oxy-l,2-ethanediyl), alpha-phenyl-omega-hydroxy, styrenated.
  • nonionic dispersing agents also named nonionic tenside
  • nonionic tenside that can be used in the aqueous dispersed dyeing solution
  • alkoxylated preferably ethoxylated or ethoxylated and propoxylated
  • fatty acid alkyl esters preferably containing 1 to 4 carbon atoms in the alkyl chain, more particularly the fatty acid methyl esters.
  • the nonionic low alkoxylated alcohol dispersing agents can be used to reduce surface tension, wet the soil particulate to allow penetration of the use solution, separation of the soil.
  • the alkoxylated alcohol dispersing agents mentioned above includes end caped alkoxylated alcohol dispersing agents.
  • Exemplary nonionic low alkoxylated alcohol dispersing agents that can be used are alkoxylated alcohols containing 1 to 4 ethylene oxide groups (1-4EO), 1 to 4 butylene oxide groups (1-4BO), 1 to 4 propylene oxide groups (1-4PO), end caped alkoxylated alcohol dispersing agents thereof or mixtures thereof.
  • Advantageously low alkoxylated alcohols useful according to the invention are particularly primary and/or branched alcohols, preferably containing 8 to 18 carbon atoms, and containing 1 to 4 ethylene oxide groups (1-4EO), 1 to 4 butylene oxide groups (1-4BO), 1 to 4 propylene oxide groups (1-4PO), end caped alkoxylated alcohol dispersing agents thereof or may contain a mixture.
  • the alcohol radical may be linear, branched, or may contain a mixture.
  • Exemplary nonionic higher alkoxylated alcohol dispersing agents suitable for use in the aqueous dispersed dyeing solution are alkoxylated alcohols containing 5 to 40 ethylene oxide groups (5-40EO), butylene oxide groups (5-40BO), propylene oxide groups (5-40PO), preferably 6 to 30 ethylene oxide groups (6-30EO), butylene oxide groups (6-30BO), propylene oxide groups (6-30PO), further preferred 7 to 20 ethylene oxide groups (7-20EO), butylene oxide groups (7-20BO), propylene oxide groups (7-20PO), more preferred 8 to 10 ethylene oxide groups (8-10EO), butylene oxide groups (8-10BO), propylene oxide groups (8-10PO), and most preferred 8 ethylene oxide groups (8EO), butylene oxide groups (8BO), propylene oxide groups (8PO) groups, end caped alkoxylated alcohol dispersing agents thereof, or mixtures thereof.
  • Advantageously higher alkoxylated alcohols useful in the composition of the invention are particularly linear and/or branched alcohols, preferably containing 8 to 18 carbon atoms, and 5 to 40 ethylene oxide groups (5-40EO), butylene oxide groups (5-40BO), propylene oxide groups (5-40PO), preferably 6 to 30 ethylene oxide groups (6-3 OEO), butylene oxide groups (6- 30BO), propylene oxide groups (6-30PO), further preferred 7 to 20 ethylene oxide groups (7- 20EO), butylene oxide groups (7-20BO), propylene oxide groups (7-20PO), more preferred 8 to 10 ethylene oxide groups (8-1 OEO), butylene oxide groups (8-10BO), propylene oxide groups (8- 10PO), and most preferred 8 ethylene oxide groups (8EO), butylene oxide groups (8BO), propylene oxide groups (8PO), end caped alkoxylated alcohol dispersing agents thereof, or may contain a mixture.
  • the alcohol radical may be linear, branched, or may contain a mixture. Particularly preferred are higher alkoxylated alcohols, preferably alcohol ethoxylates with linear or branched radicals of alcohols with 12 to 18 carbon atoms, e.g.
  • coco-, palm-, tallow- or oleyl alcohol containing 8 to 18 carbon atoms, and 5 to 40 ethylene oxide groups (5- 40EO), butylene oxide groups (5-40BO), propylene oxide groups (5-40PO), preferably 6 to 30 ethylene oxide groups (6-3 OEO), butylene oxide groups (6-3 OBO), propylene oxide groups (6- 30PO), further preferred 7 to 20 ethylene oxide groups (7-20EO), butylene oxide groups (7- 20BO), propylene oxide groups (7-20PO), more preferred 8 to 10 ethylene oxide groups (8- 10EO), butylene oxide groups (8-1 OBO), propylene oxide groups (8-10PO), and most preferred 8 ethylene oxide groups (8EO), butylene oxide groups (8BO), propylene oxide groups (8PO), end caped alkoxylated alcohol dispersing agents thereof, or may contain a mixture.
  • isotridecyl alcohol in the composition of the invention with 6EO to 14EO, 6PO to 14PO, 6BO to 14BO, preferably 7EO to 10EO, 7PO to 10PO, 7BO to 10BO, and most preferred 8EO, 8PO, 8BO, or may contain a mixture.
  • higher alkoxylated alcohols can be used with 5EO, 6EO, 7EO, 8EO, 9EO, 10EO, 11EO, 12EO, 13EO, 14EO, 15EO, 16EO,17EO, 18EO, 19EO, 20EO, 21EO, 22EO, 23EO, 24EO or 25EO, 5PO, 6PO, 7PO, 8PO, 9PO, 10PO, 1 IPO, 12PO, 13PO, 14PO, 15PO, 16PO,17PO, 18PO, 19PO, 20PO, 21PO, 22PO, 23PO, 24PO or 25PO, 5BO, 6BO, 7BO, 8BO, 9BO, 10BO, 11BO, 12BO, 13BO, 14BO, 15BO, 16BO,17BO, 18BO, 19BO, 20BO, 21BO, 22BO, 23BO, 24BO or 25BO, 5BO, 6BO, 7BO, 8BO, 9BO, 10BO, 11BO, 12BO, 13BO, 14BO, 15BO, 16BO,17BO, 18BO, 19BO, 20BO, 21BO, 22
  • fatty alcohols containing more than 12 EO, 12 PO, 12 BO may also be used.
  • fatty alcohols are tallow fatty alcohol containing 14 EO, 25 EO, 30 EO or 40 EO, 14 PO, 25 PO, 30 PO or 40 PO, 14 BO, 25 BO, 30 BO or 40 BO and end caped alkoxylated alcohol dispersing agents thereof.
  • the degrees of 5EO to 40EO, 5PO to 40PO, 5BO to 40BO preferably 6EO or 30EO, 6PO or 30PO, 6BO or 3 OBO, further preferred 7EO to 20EO, 7PO to 20PO, 7BO to 20BO,more preferred 8EO to 10 EO, 8PO to 10 PO, 8BO to 10 BO and most preferred 8EO, 8PO, 8BO alkoxylation mentioned are statistical mean values, which for a special product, may be either a whole number or a fractional number.
  • the degrees of 5EO to 40EO, 5PO to 40PO , 5BO to 40BO preferably 6EO or 30EO, 6PO or 30PO , 6BO or 30BO further preferred 7EO to 20EO, 7PO to 20PO , 7BO to 20BO, more preferred 8EO to 10 EO, 8PO to 10 PO, 8BO to 10 BO and most preferred 8EO, 8PO, 8BO alkoxylation mentioned may be either a whole number or a fractional number.
  • the alkoxylation grade mentioned may be a whole number.
  • Preferred higher alkoxylated alcohols have a narrow homolog distribution (narrow range ethoxylates, NRE).
  • Further dispersing agents include alkoxylated long chain fatty acid amides where the fatty acid has 8-20 carbon atoms and the amide group is alkoxylated with 1-20 ethylene oxide, propylene oxide and/or butylene oxide units.
  • a further class of nonionic dispersing agents which can be used in the aqueous dispersed dyeing solution, is that of the alkyl polyglycosides (APG).
  • APG alkyl polyglycosides
  • Suitable alkyl polyglycosides satisfy the general Formula RO(G)z where R is a linear or branched, particularly 2-methyl-branched, saturated or unsaturated aliphatic radical containing 8 to 22 and preferably 12 to 18 carbon atoms and G stands for a glycose unit containing 5 or 6 carbon atoms, preferably glucose.
  • the degree of oligomerization z is a number between 1.0 and 4.0 and preferably between 1.1 and 1.4.
  • Silicone containing nonionic dispersing agents such as the ABIL B8852 or Silwet 7602, can also be used.
  • An exemplary silicone-containing dispersing agent is silicone polybutane.
  • amine oxide dispersing agents include: dimethyldodecylamine oxide, dimethyltetradecylamine oxide; ethylmethyltetradecylamine oxide, cetyldimethylamine oxide, dimethylstearylamine oxide, cetylethylpropylamine oxide, diethyldodecylamine oxide, diethyltetradecylamine oxide, dipropyldodecylamine oxide, lauryl dimethyl amine oxide, bis- (2- hydroxy ethyl) dodecylamine oxide, bis- (2-hydroxyethyl)-3-dodecoxy-l- hydroxypropyl amine oxide, (2-hydroxypropyl) methyltetradecylamine oxide, dimethyloleyamine oxide, dimethyl- (2- hydroxydodecyl) amine oxide, and the corresponding decyl, hexadecyl and octadecyl homologs of the above compounds.
  • Additional nitrogen-containing dispersing agents include ethoxylated primary alkyl amines where the alkyl group has 10-20 carbon atoms and the amine is ethoxylated with 2-20 ethylene oxide units.
  • non-ionic dispersing agents derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine are also useful.
  • non-ionic dispersing agents derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine are also useful.
  • Suitable nonionic dispersing agents include the polyoxyethylene-polyoxypropylene condensates, which are sold by BASF under the trade name 'Pluronic', polyoxyethylene condensates of aliphatic alcohols/ethylene oxide condensates having from 1 to 30 moles of ethylene oxide per mole of coconut alcohol; ethoxylated long chain alcohols sold by Shell Chemical Co.
  • alkanolamides such as the monoalkoanolamides, dialkanolamides and the ethoxylated alkanolamides, for example coconut monoEthanolamide, lauric isopropanolamide and lauric diEthanolamide
  • amine oxides for example dodecyldimethylamine oxide
  • non-ionic dispersing agents include alkylphenol alkoxylates, and amine oxides such as alkyl dimethylamine oxide or bis (2- hydroxyethyl) alkylamine oxide.
  • the additional nonionic dispersing agents can be provided in the aqueous dispersed dyeing solutionin an amount of > 0 wt.-% to ⁇ 40 wt.-%, preferably > 0.1 wt.-% to ⁇ 35 wt.-%, further preferred > 0.5 wt.-% to ⁇ 32 wt.-%, and more preferred 1.0 wt.-% to 30 wt.-%, based on the weight of all components of the total composition.
  • anionic dispersing agents also named nonionic tenside
  • organic carboxylates organic sulfonates, organic sulfates, organic phosphates and the like, particularly linear alkylaryl sulfonates, such as alkylarylcarboxylates, alkylarylsulfonates, alkylarylphosphates, and the like.
  • linear alkyl benzyl sulfonates LPS
  • alpha olefin sulfonates AOS
  • alkyl sulfates alkyl sulfates
  • secondary alkane sulfonates secondary alkane sulfonates.
  • the anionic dispersing agents can be provided in the aqueous dispersed dyeing solutionin an amount of > 0 wt.-% to ⁇ 40 wt.-%, preferably > 0.1 wt.-% to ⁇ 35 wt.-%, further preferred > 0.5 wt.-% to ⁇ 32 wt.-%, and more preferred 1.0 wt.-% to 30 wt.-%, based on the weight of all components of the total composition.
  • aqueous dispersed dyeing solution comprises a cationic dispersing agent, also named cationic tenside.
  • Suitable cationic dispersing agents include quaternary ammonium compounds having the formula of RR'R" R"'N + X , where R, R', R" and R'" are each a C1-C24 alkyl, aryl or arylalkyl group that can optionally contain one or more P, O, S or N heteroatoms, and X is F, Cl, Br, I or an alkyl sulfate.
  • Additional preferred cationic dispersing agents include ethoxylated and/or propoxylated alkyl amines, diamines, or triamines.
  • R, R', R" and R'" can independently include, individually or in combination, substituents including 6 to 24 carbon atoms, preferably 14 to 24 carbon atoms, and more preferably, 16 to 24 carbon atoms.
  • R, R', R" and R'" can independently be linear, cyclic, branched, saturated, or unsaturated, and can include heteroatoms such as oxygen, phosphorous, sulfur, or nitrogen. Any two of R, R', R" and R'” can form a cyclic group. Any one of three of R, R', R" and R'" can independently can be hydrogen.
  • X is preferably a counter ion and preferably a non-fluoride counter ion. Exemplary counter ions include chloride, bromide, methosulfate, ethosulfate, sulfate, and phosphate.
  • the quaternary ammonium compound includes alkyl ethoxylated and/or propoxylated quaternary ammonium salts (or amines).
  • the alkyl group contains between about 6 and about 22 carbon atoms and can be saturated and/or unsaturated.
  • the degree of alkoxylation is preferably between about 2 and about 20, and/or the degree of propoxylation is preferably between about 0 and about 30.
  • the quaternary ammonium compound includes an alkyl group with about 6 to about 22 carbon atoms and a degree of alkoxylation between about 2 and about 20.
  • the cationic dispersing agents can be provided in the aqueous dispersed dyeing solutionin an amount of > 0 wt.-% to ⁇ 40 wt.-%, preferably > 0.1 wt.-% to ⁇ 35 wt.-%, further preferred > 0.5 wt.-% to ⁇ 32 wt.-%, and more preferred 1.0 wt.-% to 30 wt.-%, based on the weight of all components of the total composition.
  • the aqueous dispersed dyeing solution is preferably free of amphoteric dispersing agents.
  • amphoteric dispersing agents examples include capryloamphopropionate, disodium lauryl B-iminodipropionate, and cocoamphocarboxypropionate, and disodium octylimino dipropionate.
  • the amphoteric dispersing agents can be provided in the composition in an amount of > 0 wt.-% to ⁇ 40 wt.-%, preferably > 0.1 wt.-% to ⁇ 35 wt.-%, further preferred > 0.5 wt.-% to ⁇ 32 wt.-%, and more preferred 1.0 wt.-% to 30 wt.-%, based on the weight of all components of the total composition.
  • the solubilizer is selected different to the dispersing agent and may be used in addition to the dispersing agent.
  • the solubilizer is at least partially soluble at 23° C and may be selected from the group comprising a Ci to Ce alcohol, C2 to C20 organic acid, C3 to Ce ketone, C3 to C5 aldehyde, Ci to Ce alkyl, C3 to Ce ester, alkylene glycol alkyl ether, glycol alkyl ether,; preferably glycol and glycol oligomers, Ethanol, acetone, formic or acetic acid, dimethylformamide or dimethylsulfoxide.
  • the solubilizer may be a compound according to the following formula R'— [(0(CFh)m)n— ]OH, wherein R' is an ethyl, propyl or butyl radical, m is 2, 3 or 4, and n is 1, 2 or 3, with the proviso that where R' is butyl m is 2 or 4.
  • the solubilizer may be selected from the group consisting of ethylene glycol butyl ether, diethylene glycol ethylether, diethylene glycol butylether, propylene glycol propylether, dipropylene glycol propyl ether and tripropylene glycol propylether.
  • the solubilizer may be a compound according to the following formula H— [(0(CH 2 )m)n— ]OH, where m is 2, 3 or 4 and n is 1, 2, or 3.
  • the solubilizer may be selected from the group consisting of diethylene glycol, triethylene glycol and 1 ,4 butanediol.
  • the solubilizer forms a homogenous solution with water.
  • the carrier agent is selected different to the dispersing agent and the solubilizer and may be used in addition to the dispersing agent.
  • the aqueous dispersed dyeing solution further comprises a carrier agent.
  • the aqueous dispersed dyeing solution may comprise in addition a carrier agent, wherein the carrier agent is preferably selected from the group comprising aromatic esters such as phthalic acid esters, polyphenylether, phenoles, aromatic alcohols, aromatic ketones, aryl halides, such as halogenized benzene, halogenzide toluene; N-alkylphthalimide, methylnaphthaline, diphenyle, diphenylethere, naphtholether, and oxybiphenyle.
  • the carrier agent does not form a homogenous solution with water.
  • the carrier agent may decrease the time that is used for dyeing and/or enhance the penetration capacity of the organic aromatic dye.
  • the temperature of the aqueous dispersed dyeing solution is adjusted according to specific properties of the synthetic polar-polymer material.
  • the temperature of the aqueous dispersed dyeing solution exposed to the outer surface of the synthetic polar-polymer material may be adjusted such that the temperature of the aqueous dispersed dyeing solution is higher or same than the glass-transition temperature T g of the synthetic polar-component of the synthetic polar-polymer material to be colored; and/or the aqueous dispersed dyeing solution exposing the synthetic polar-polymer material may have a temperature lower than the heat deflection temperature of the synthetic polar-polymer material to be colored. This may have the advantages that distortion or deforming of the synthetic polar- polymer material may be avoided.
  • the heat deflection temperature also called heat distortion temperature may be the temperature at which synthetic polar-polymer material deforms under a specified load. It may be determined by the following test procedure outlined in ASTM D648. The test specimen is loaded in three-point bending in the edgewise direction. The outer fiber stress used for testing is either 0.455 MPa or 1.82 MPa, and the temperature is increased at 2 °C/min until the specimen deflects 0.25 mm.
  • the heat deflection temperature also called heat distortion temperature (HDT) may be measured according to DIN EN ISO 75-1 to 3.
  • the test specimen is loaded according to the three-point bending principle, which means that the bending moment is not constant over the length of the test specimen, but rather increases from the support points to the point of application of the individual load.
  • the individual load is dimensioned so that a maximum bending stress of 1.80 MPa (method A), 0.45 MPa (method B) or 8.0 MPa (method C) is present.
  • the heating takes place at a heating rate of 2 °C/min, with air or silicone oil usually being used as the heat carrier.
  • the step of exposing the outer surface of the synthetic polar-polymer material to the aqueous dispersed dyeing solution may comprises:
  • the specific way how the outer surface of the synthetic polar-polymer material is exposed to the aqueous dispersed dyeing solution may be dependent on the article made of the synthetic polar-polymer material.
  • the article may be dipped into the aqueous dispersed dyeing solution in such a fashion that the inner surface of the bottle may not be exposed to the aqueous dispersed dyeing solution.
  • it may be advantageous to flow coat the outer surface of the synthetic polar-polymer material with the aqueous dispersed dyeing solution.
  • These method steps may increase and/or homogenize the migration of the organic aromatic dye into the synthetic polar-polymer material.
  • the synthetic polar-polymer material which is exposed to the aqueous dispersed dyeing solution, may have a temperature in the range of about > 40° C to about ⁇ 150° C, preferably the synthetic polar-polymer material, which is exposed to the aqueous dispersed dyeing solution, may have a temperature about > 40° C and lower than the heat deflection temperature of the synthetic polar-polymer material. It may be preferably that the synthetic polar- polymer material may have a temperature that corresponds to the temperature of the aqueous dispersed dyeing solution +/- 10 °C.
  • the temperature difference between the synthetic polar-polymer material and the aqueous dispersed dyeing solution may not be higher than 10 °C. This may reduce unwanted effects in the synthetic polar-polymer material caused by a fast increase or decrease of the temperature.
  • the synthetic polar-polymer material may have a temperature lower than the heat deflection temperature of the synthetic polar-polymer material.
  • the synthetic polar-polymer material does not deflect and/or deform when exposed to the conditions of the aqueous dispersed dyeing solution.
  • the synthetic polar-polymer material may be partially cooled while being exposed to the aqueous dispersed dyeing solution.
  • the bottle may be dipped into the aqueous dispersed dyeing solution in such a fashion that the inner surface of the bottle may not be exposed to the aqueous dispersed dyeing solution.
  • the inner surface of the bottle may be cooled, while the outer surface of the bottle is exposed to the aqueous dispersed dyeing solution.
  • the synthetic polar-polymer material may be formed in a molding process, a compression molding process, an extruding process, a thermoforming process, a blowing process and/or a 3D-printing process, thereafter exposed to the aqueous dispersed dyeing solution; preferably the synthetic polar-polymer material may be directly exposed, without cooling, to the aqueous dispersed dyeing solution.
  • the synthetic polar-polymer material may be further formed in a compression molding, an injection molding, a rotational molding, an extrusion, an injection and/or extrusion blow molding, and/or casting process.
  • the method of forming the synthetic polar-polymer material may not be critical to the method of reversibly and selectively dyeing the synthetic polar-polymer material.
  • the synthetic polar-polymer material may be formed in another manufacturing process including all other manufacturing processes not explicitly listed here for the manufacturing of plastic parts.
  • the synthetic polar-polymer material preferably at least one outer surface of the synthetic polar-polymer material, may be exposed to the aqueous dispersed dyeing solution for about > 1 second to about ⁇ 60 minutes, preferably about > 3 seconds to about ⁇ 30 minutes, in addition preferred about > 5 seconds to about ⁇ 10 minutes, and also preferred about > 10 seconds to about ⁇ 1 minute, or about > 15 seconds to about ⁇ 30 seconds.
  • the synthetic polar-polymer material preferably at least one outer surface of the synthetic polar-polymer material, may be exposed to the aqueous dispersed dyeing solution for about > 1 second to about ⁇ 10 minutes, preferably about > 2 seconds to about ⁇ 8 minutes, in addition preferred about > 5 seconds to about ⁇ 6 minutes, and also preferred about > 10 seconds to about ⁇ 4 minutes, or about > 15 seconds to about ⁇ 2 minutes.
  • the outer surface of a synthetic polar-polymer material is completely colored at about > 1 second to about ⁇ 10 minutes, preferably about > 2 seconds to about ⁇ 8 minutes, in addition preferred about > 5 seconds to about ⁇ 6 minutes, and also preferred about > 10 seconds to about ⁇ 4 minutes, or about > 15 seconds to about ⁇ 2 minutes, that means the colorized surface of the synthetic polar-polymer material has a color defined by the organic aromatic dye or mixtures thereof.
  • the synthetic polar-polymer material may be withdrawn at a specific rate from the aqueous dispersed dyeing solution, including a rate sufficient to effect a dyeing gradient. Therefore, the portion of the synthetic polar-polymer material that remains in the aqueous dispersed dyeing solution longest may contain the most organic aromatic dye per unit volume so that it exhibits the darkest color tint.
  • the thickness of the layer that is colored may be about 1% to about 100% for a single layer, or about 0.1% to about 99% for a multilayer, regardless of the total thickness, or about 0.1 pm to about 1000 pm, or preferably about 1% to about 40%.
  • the thickness of the layer that is completely colored may be about 1 pm to about 50 pm, more preferably about 5 pm to about 25 pm.
  • the layer thickness of the synthetic polar-polymer material that is colorized by the method according to the present invention may be about > 0.1 pm, preferably of about > 1 pm to about ⁇ 1000 pm, preferably the synthetic polar-polymer material is homogenously colored.
  • the layer thickness of the synthetic polar-polymer material that is colorized by the method according to the present invention may be about > 0.1 pm, preferably of about > 1 pm to about ⁇ 1000 pm, with a dyeing grade of 0.1% to ⁇ 100%, preferably > 1% to ⁇ 90%.
  • the additivated layer is completely colored.
  • the total thickness of the layer is may be about 3 mm, but the dye penetrates only about 2 pm to about 20 pm.
  • the layer is 25% colorized of a thickness of 2mm, or the layer is 50% colorized of a thickness of 100pm.
  • the thickness and % of colorization is depending on the article that is colorized by a method according to the invention.
  • the layer thickness of the polar-polymer material that is colored by the process according to the invention may be about > 1 pm to about ⁇ 50 pm, preferably about > 2 pm to about ⁇ 30 pm, further preferred about > 3 pm to about ⁇ 20 pm, also preferred about > 4 pm to about ⁇ 15 pm, in addition preferred about > 5 pm to about ⁇ 12 pm and furthermore preferred about > 6 pm to about ⁇ 10 pm, wherein the colorized layer of the synthetic polar-polymer material has a color defined by the organic aromatic dye or mixtures thereof used.
  • the synthetic polar-polymer material may be exposed to the aqueous dispersed dyeing solution for about > 1 second to about ⁇ 60 minutes, preferably about > 3 seconds to about ⁇ 30 minutes, in addition preferred about > 5 seconds to about ⁇ 10 minutes, and also preferred about > 10 seconds to about ⁇ 1 minute, or about > 15 seconds to about ⁇ 30 seconds; wherein the layer thickness of the polar-polymer material that is colored by the process according to the invention is about > 1 pm to about ⁇ 50 pm, preferably about > 2 pm to about ⁇ 30 pm, further preferred about > 3 pm to about ⁇ 20 pm, also preferred about > 4 pm to about ⁇
  • the colorized layer of the synthetic polar-polymer material has a color defined by the organic aromatic dye or mixtures thereof used.
  • the synthetic polar-polymer material may be exposed to the aqueous dispersed dyeing solution for about > 1 second to about ⁇ 10 minutes, preferably about > 2 seconds to about ⁇ 8 minutes, in addition preferred about > 5 seconds to about ⁇ 6 minutes, and also preferred about > 10 seconds to about ⁇ 4 minutes, or about > 15 seconds to about ⁇ 2 minutes; wherein the layer thickness of the polar-polymer material that is colored by the process according to the invention is about > 1 pm to about ⁇ 50 pm, preferably about > 2 pm to about ⁇ 30 pm, further preferred about > 3 pm to about ⁇ 20 pm, also preferred about > 4 pm to about ⁇ 15 pm, in addition preferred about > 5 pm to about ⁇ 12 pm and furthermore preferred about > 6 pm to about ⁇ 10 pm, wherein the colorized layer of the synthetic polar-polymer material has a color defined by the organic aromatic dye or mixtures thereof used.. pH
  • the result of the dyeing process may be influenced by the pH of the aqueous dispersed dyeing solution.
  • the aqueous dispersed dyeing solution may have a pH in the acidic range.
  • the aqueous dispersed dyeing solution has a pH in the range of about > 2.5 and about ⁇ 6.5 or of about > 3.2 and about ⁇ 6.5, preferably a pH in the range of about > 3.4 and about ⁇ 6; in addition preferred a pH in the range of about > 3.5 and about ⁇ 5.5 and also preferred a pH in the range of about > 4 and about ⁇ 5. It may be possible to reduce the pH of the aqueous dispersed dyeing solution by adding acetic acid to the aqueous dispersed dyeing solution.
  • the colorizing speed of the synthetic polar-polymer material can be significant increased by a pH ⁇ 7.
  • the colorizing speed of the synthetic polar-polymer material seems to be highest at a pH range of the aqueous dispersed dyeing solution of about > 2.5 and about ⁇ 6, in particular at a pH range of about > 3.5 and about ⁇ 5.
  • the colorizing time for colorizing a layer thickness of the polar-polymer material that is colored by the process according to the invention can be of about > 1 pm to about ⁇ 50 pm, preferably about > 2 pm to about ⁇ 30 pm, further preferred about > 3 pm to about ⁇ 20 pm, also preferred about > 4 pm to about ⁇ 15 pm, in addition preferred about > 5 pm to about ⁇ 12 pm and furthermore preferred about > 6 pm to about ⁇ 10 pm, is ⁇ 10 minutes, preferably about > 2 seconds to about ⁇ 8 minutes, in addition preferred about > 5 seconds to about ⁇ 6 minutes, and also preferred about > 10 seconds to about ⁇ 4 minutes, or about > 15 seconds to about ⁇ 2 minutes.
  • the dyeing process is rather fast.
  • the duration of the exposure the migration depth of the migration of the organic aromatic dye into the synthetic polar-polymer material and/or the concentration of the organic aromatic dye in the synthetic polar-polymer material may be varied. Therefore, the color appearance of the colored synthetic polar-polymer material may also vary according to the duration of exposure. For example the color of a colored synthetic polar-polymer material that has been exposed to the aqueous dispersed dyeing solution for ⁇ 10 minutes may be more intense than the color of a colored synthetic polar-polymer material that has been exposed to the aqueous dispersed dyeing solution for ⁇ 5 minutes.
  • the aqueous dispersed dyeing solution may comprise: - about > 0.1 wt.-% to about ⁇ 15 wt.-% at least one organic aromatic dye having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol;
  • the polar-polymer material can comprise at least one or more layers.
  • the polar-polymer material can comprises a multi-layer.
  • the layers may be differently composed.
  • One layer of the polymer material may have a content of polar components and non-polar polymers, wherein the content of the polar components are less than about 5 wt.-%, preferably about ⁇ 3 wt.-%, further preferred about ⁇ 2 wt.-% and in addition preferred about ⁇ 0.5 wt.-% or about ⁇ 0.1 wt.-% and about > 90 wt.-%, preferably about > 95 wt.-%, more preferably preferably about > 99.5 wt.-% of non-polar components, such as non-polar polymer and/or non-polar oligomer cannot be colorized by the method according to the present invention.
  • a two layer polar-polymer material such as a bottle, wherein the outer surface directed outwards is of a polar-polymer material comprises about > 0.5 wt.-%, preferably about > 5 wt.-%, more preferably > 10 wt.-%, of polar components, such as synthetic polar polymer, synthetic polar oligomer and/or polar additive, can be colored by the method according to the invention, where else the inner layer facing to the inside of the bottle, which is a layer comprising less than about 5 wt.-%, preferably about ⁇ 3 wt.-%, further preferred about ⁇ 2 wt.-% and in addition preferred about ⁇ 1 wt.-%, and more preferably ⁇ 0.5 wt.-%, or about > 0 to ⁇ 0.1 wt.-% of a polar component and about > 90 wt.-%, preferably about > 95 wt.-%, more preferably about > 99.5
  • the inner layer that is supposed to be in contact to the filling of the package may be free of the organic aromatic dye.
  • a synthetic polar-polymer material may comprises at least two layers, wherein at least a first layer is of a polar-polymer material, that comprises about >
  • polar components such as synthetic polar polymer, synthetic polar oligomer and/or polar additive
  • the article may be selected from the group comprising a sheet, a foil, a tube, a container, a part, a bottle and preferably the article may be selected from the group comprising computer face-plates, keyboards, bezels and cellular phones, color coded packaging and containers of all types, including ones for industrial components, residential and commercial lighting fixtures and components therefor, such as sheets, used in building and in construction, tableware, including plates, cups and eating utensils, small appliances and their components, optical and sun-wear lenses, as well as decorative films including such films that are intended for use in film insert molding.
  • the article may not be selected from the group comprising a fiber, a woven fabric, and a knitted fabric.
  • the present invention further relates to the colored synthetic polar-polymer material, wherein the synthetic polar-polymer material, preferably the outer surface of the synthetic polar- polymer material, is colored by the above described method.
  • the synthetic polar-polymer material preferably the outer surface of the synthetic polar- polymer material
  • the colored synthetic polar-polymer material may comprise at least one synthetic polar-component layer and at least one non-polar-component layer, wherein at least one layer or outer surface of the synthetic polar-component layer is colored by the above described method, wherein the non-polar-component layer is not colorable by the above described method.
  • the colored synthetic polar-polymer material may have a layered structure, comprising the synthetic polar-component layer and the non-polar-component layer. Only the synthetic polar-component layer may be colorable with the above described method but not the non-polar-component layer. Therefore, by adjusting the polarity of the different layers it may be possible to selectively color the desired layers while the other layers remain colorless.
  • the dyeing process is based on migration of the organic aromatic dye into the synthetic polar-polymer material.
  • the outer layer of the synthetic polar- polymer material gets colored.
  • a colored synthetic polar-polymer material may be provided, wherein at least a layer thickness of about > 0.1 pm of an outer layer of the colored synthetic polar-polymer material is homogenous colored. Homogeneous coloration of the outer layer of the synthetic polar-polymer material may be achieved by having the same amount of the organic aromatic dye per area of the outer surface of the synthetic polar-polymer material.
  • the organic aromatic dye may be essentially homogenously distributed in the colored part or layer of the synthetic polar-polymer material, meaning that that for the eye of a human being the colored outer surface or the colored part or the colored layer of the synthetic polar-polymer material appear uniformly colored without color variations.
  • the outer surface may be
  • the colored surface may be homogenously colored when no significant color fluctuations may be visible by the human eye.
  • the color differences, given in AE* ab according to the International Commission on Illumination (CIE), over the outer surface of the colored synthetic polar-polymer material may be about ⁇ 2.
  • the concentration of the organic aromatic dye in at least one colored layer of the synthetic polar-polymer material, colored by the above described method, wherein the colored layer has a thickness of about > 0.1 pm may be 0.00001 wt.-% to about ⁇ 5 wt.-%, based on the total weight of said colored layer.
  • the colored synthetic polar- polymer material it is referred to the method for reversible and selective dyeing the synthetic polar-polymer material, the article comprising at least one colored synthetic polar-polymer material, the examples and the further description.
  • the present invention further relates to an article comprising at least one colored synthetic polar-polymer material as described above and colored by the method as described above.
  • the present invention solves an important object how to design a dyeing process to be environmentally friendly.
  • RGB color space works on the principle of the additive color space. This means that it reproduces the entire color range by mixing the basic colors red, green and blue.
  • the RGB color space can be found in all self-illuminating systems, such as monitors or television screens. All possible colors are defined by their red, green and blue components and mapped accordingly by the overlay of colored light.
  • the Lab color space is based on counter-color theory. This is based on the assumption that three separate chemical processes take place in the human retina, which always contain two opposite colors, the two opposite colors striving for balance with one another. An example pair would be the combination of blue and yellow. Lab is used, for example, for photo editing software. While the RGB color space is device-dependent, it is not the Lab color space. RGB includes - regardless of the device - all potentially possible colors, which above all enables the conversion of color definitions from one device to the other.
  • the Lab - measuring device The Lab - measuring device
  • the Lab is measured with a - Spectrometer Konika-Minolta CM-3600A - according to the guideline of the INSTRUCTION MANUAL CM-3600A ( ⁇ 2011-2013 KONICA MINOLTA, INC ).
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 92 wt- % HDPE (MFI 20) and 8 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5 :
  • dispersing agent of 30 g Efka® 4300 (acrylic block-copolymer) obtainable by BASF SE and 160 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 80° C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 8 minutes at a pH of 2.9.
  • the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 60/6/-43 or converted to RGB: 98/145/220
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 92 wt- % HDPE (MFI 20) and 8 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5 :
  • dispersing agent of 25 g Efka® 4300 (acrylic block-copolymer) obtainable by BASF SE and 160 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 85° C at a pH of 3.2.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 7 minutes. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration dept of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 6 pm and the achieved coloration is determined to Lab: 55/6/-43 or converted to RGB: 84/132/206
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 92 wt- % HOPE (MFI 20) and 8 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5 :
  • dispersing agent of 23 g Efka® PU 4050 is a modified
  • polyurethane obtainable by BASF SE and 240 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90 C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 6 minutes at a pH of 3.9. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 8 pm and the achieved coloration is determined to Lab: 32/7/-43 or converted to RGB: 0/76/143.
  • Example 4 A translucent white (like frosted glass) polar polymer material layer of 90 wt.-% HDPE (MFI 20) and 10 wt.-% of poly e-Capro lactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5:
  • dispersing agent of 25 g Efka® PEI 4050 (is a modified polyurethane) obtainable by BASF SE and 240 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 95 C.
  • the translucent white (like frosted glass) polar polymer material layer is exposed to the aqueous dyeing solution for about 8 minutes at a pH of 3.5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 10 pm and the achieved coloration is determined to Lab: 13/16/- 37 or converted to RGB: 0/30/87.
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 95 wt- % HDPE (MFI 20) and 5 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula Al :
  • dispersing agent of 30 g Efka® 4300 (acrylic block- copolymer) obtainable by BASF SE and 200 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90° C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 5 minutes at a pH of 3.5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula Al) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 70/-4/-6 or converted to RGB: 157/174/182
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 93 wt- % HDPE (MFI 20) and 7 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A2:
  • dispersing agent of 28 g Efka® 4300 (acrylic block- copolymer) obtainable by BASF SE and 120 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 100° C at a pH of 4.2.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 9 minutes. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A2) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 97/- 21/94 or converted to RGB: 255/254/0
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 95 wt- % HOPE (MFI 20) and 5 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A3 :
  • modified polyurethane obtainable by BASF SE and 160 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 80° C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 6 minutes at a pH of 3.8. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A3) in the polar polymer material layer is at least 3 pm and the achieved coloration is determined to Lab: 82/31/-6 or converted to RGB: 255/182/215
  • a translucent white (like frosted glass) polar polymer material layer of 90 wt.-% HDPE (MFI 20) and 10 wt.-% of poly e-Capro lactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A10:
  • polyurethane obtainable by BASF SE and 350 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90° C.
  • the translucent white (like frosted glass) polar polymer material layer is exposed to the aqueous dyeing solution for about 5 minutes at a pH of 5.5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A10) in the polar polymer material layer is at least 10 pm and the achieved coloration is determined to Lab: 57/73/37or converted to RGB: 255/56/76
  • a translucent white (like frosted glass) polar polymer material layer of a blend of 95 wt- % HOPE (MFI 20) and 5 wt.-% of poly e-Caprolactone (MFI 2-4 and MW about 80.000) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5 :
  • dispersing agent of 32 g Efka® 4300 (acrylic block-copolymer) obtainable by BASF SE, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 80° C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 9 minutes at a pH of 2.9. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 4 pm and the achieved coloration is determined to Lab: 73/6A35 or converted to RGB: 73L5/-35
  • An article comprising two layers, wherein the first layer is a translucent white (like frosted glass) polar polymer material of a blend of 95 wt.-% HDPE (MFI 20) and 5 wt.-% of poly e-Capro lactone (MFI 2-4 and MW about 80.000) and the second layer is a non-polar component layer comprising 100 wt.-% HDPE (MFI 20).
  • the article which has a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula Al :
  • the article is exposed to the aqueous dispersed dyeing solution for about 5 minutes at a pH of 3.5. Thereafter the article is removed from the aqueous dispersed dyeing solution and the article is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the first layer, i.e. the translucent white (like frosted glass) polar polymer material layer is colored wherein the second layer i.e. the non-polar component layer is not colored.
  • the homogenous penetration depth of the organic aromatic dye (formula Al) in the first layer is at least 5 pm and the achieved coloration is determined to Lab: 81/-3/6 or converted to RGB: 189/203/212
  • a translucent white (like frosted glass) polar polymer material of a blend of 90 wt.-% HOPE (MFI 20) and 10 wt.-% of a low melting lubricated polyamide 6/66 copolymer (melting point 195 - 198°C, lubricant 300 - 500mg/kg) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5: dispersing agent of 20 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 240 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 20 minutes at a pH of 3.9. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 40/16/- 60 or converted to RGB: 0/92/193.
  • polyurethane obtainable by BASF SE and 280 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 95°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 30 minutes at a pH of 3.5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 7 pm and the achieved coloration is determined to Lab: 30/16/- 60 or converted to RGB: 0/69/166.
  • a translucent white (like frosted glass) polar polymer material of a blend of 92 wt.-% HOPE (MFI 20) and 8 wt.-% of a polyvinylalkohol (melt viscosity 12 g/lOmin @ 190°C/21,6kg) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5:
  • polyurethane obtainable by BASF SE and 360 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 10 minutes at a pH of 4,2. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 8 pm and the achieved coloration is determined to Lab: 32/-35A 45 or converted to RGB: 0/92/146.
  • a translucent white (like frosted glass) polar polymer material of a blend of 98 wt.-% HDPE (MFI 20) and 2 wt.-% of a 1 : 1 mixture of Mg and A1 stearate with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A5: dispersing agent of 32 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 280 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 97°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 20 minutes at a pH of 4,4. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A5) in the polar polymer material layer is at least 4 pm and the achieved coloration is determined to Lab: 50/6/-43 or converted to RGB: 69/120/192.
  • a translucent white (like frosted glass) polar polymer material of a blend of 85 wt.-% HDPE (MFI 20) and 15 wt.-% of a random copolymer of Ethylene and Methyl Acrylate (MA content 19 - 22%, MFI 8 g/lOmin @ 190°C, 2,16kg) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A8:
  • Efka® 4300 an acrylic block- copolymer obtainable by BASF SE and 200 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 90°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 15 minutes at a pH of 3,0. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A8) in the polar polymer material layer is at least 3 pm and the achieved coloration is determined to Lab: 85/-4/78 or converted to RGB: 243/210/46.
  • dispersing agent of 30 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 160 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 93 °C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 20 minutes at a pH of 3,3 Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A9) in the polar polymer material layer is at least 3 pm and the achieved coloration is determined to Lab: 88/- 13/58 or converted to RGB: 233/226/107.
  • a translucent white (like frosted glass) polar polymer material of a blend of 94 wt.-% HDPE (MFI 20) and 6 wt.-% of a random copolymer of Ethylene and Acrylic Acid (AA content 11%, MFI l,5g/10min, 190°C, 2,16kg) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A6:
  • dispersing agent of 29 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 160 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 93°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 12 minutes at a pH of 3,8 Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A6) in the polar polymer material layer is at least 4 pm and the achieved coloration is determined to Lab: 55/68/7 or converted to RGB: 235/65/123.
  • polyurethane obtainable by BASF SE and 240 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 95°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 10 minutes at a pH of 3,8 Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A6) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 50/61/8 or converted to RGB: 219/61/107.
  • Example 19 A translucent white (like frosted glass) polar polymer material of a blend of 95 wt.-% HDPE (MFI 20) and 5 wt.-% of a dimer Pentaerythritol derivate (melting point 190 - 200°C) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A7:
  • (A7) a dispersing agent of 30 g Efka® 4300 (an acrylic block- copolymer) obtainable by BASF SE and 280 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 95°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 15 minutes at a pH of 3,1 Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A7) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 66/6/-40 or converted to RGB: 123/161/232.
  • a dispersing agent of 32 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 200 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 93 °C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 20 minutes at a pH of 3,9. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A7) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 63/6/-38 or converted to RGB: 118/152/220.
  • a translucent white (like frosted glass) polar polymer material of a blend of 85 wt.-% HOPE (MFI 20) and 15 wt.-% of a random copolymer of Ethylene and Methyl Acrylate (MA content 19 - 22%, MFI 8 g/lOmin @ 190°C, 2,16kg) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A2:
  • Efka® 4300 an acrylic block- copolymer obtainable by BASF SE and 160 ml of a solubilizer of l-methoxy-2-propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 97°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 15 minutes at a pH of 4,2. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A2) in the polar polymer material layer is at least 5 pm and the achieved coloration is determined to Lab: 95/- 13/50 or converted to RGB: 249/245/142.
  • modified polyurethane obtainable by BASF SE and 120 ml of a solubilizer of l-methoxy-2- propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 93°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 10 minutes at a pH of 4,0 Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A3) in the polar polymer material layer is at least 4 pm and the achieved coloration is determined to Lab: 82/31/-6 or converted to RGB: 255/182/215.
  • block-copolymer obtainable by BASF SE and 320 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 95°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 13 minutes at a pH of 3,5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A3) in the polar polymer material layer is at least 6 pm and the achieved coloration is determined to Lab:
  • modified polyurethane obtainable by BASF SE and 240 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 97°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 13 minutes at a pH of 3,4. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A3) in the polar polymer material layer is at least 6 pm and the achieved coloration is determined to Lab:
  • dispersing agent of 30 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 280 ml of a solubilizer of of l-methoxy-2- propyl acetate, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 98°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 18 minutes at a pH of 3,0. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A4) in the polar polymer material layer is at least 3 pm and the achieved coloration is determined to Lab: 40/6/-43 or converted to RGB: 34/95/165.
  • a translucent white (like frosted glass) polar polymer material of a blend of 93 wt.-% HDPE (MFI 20) and 7 wt.-% of a low melting copolyester (inherent viscosity IV 0,7, glass transition temp 75°C (D1525)) with a length of 10 cm, height of 1 cm and width of 1 cm is placed in 800 ml of an aqueous dyeing solution, wherein the aqueous dyeing solution comprises 8 g of an organic aromatic dye having formula A4:
  • dispersing agent of 28 g Efka® 4300 an acrylic block-copolymer obtainable by BASF SE and 240 ml of a solubilizer of of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 97°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 20 minutes at a pH of 3,5. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A4) in the polar polymer material layer is at least 2 pm and the achieved coloration is determined to Lab: ⁇ 5/-2/- 75 or converted to RGB: 117/190/255.
  • dispersing agent of 29 g Efka® PU 4050 (is a modified polyurethane) obtainable by BASF SE and 320 ml of a solubilizer of Ethanol, wherein the aqueous dyeing solution contacting the polar polymer material has a temperature of 98°C.
  • the polar polymer material layer is exposed to the aqueous dyeing solution for about 21 minutes at a pH of 3,3. Thereafter the polar polymer material layer is removed from the aqueous dyeing solution and the colored polar polymer material layer is rinsed with water of 30° C at least 3 times to remove color residuals.
  • the homogenous penetration depth of the organic aromatic dye (formula A4) in the polar polymer material layer is at least 3 pm and the achieved coloration is determined to Lab: 50/0/-55 or converted to RGB: 0/124/213. Decoloring
  • Examples 1 to 27 may be decolorized according to examples 28 to 54 respectively. It can be taken from examples 28 to 54 that the process of the present invention is a very mild, efficient and environmental friendly method for decolorizing a colorized polar polymer material, wherein the dye is removed from the colorized polar-polymer material. Further the polar decoloring agent that absorbs/adsorbs the dye can be used to recoloring a polymer material by adding thereto. Further, the decolorized polar polymer material can be reused for coloring. That means the color agent as well as the synthetic and/or non-synthetic polar-polymer material can be recycled.
  • mixtures of polar polymers, polar oligomers or polar additives with high affinity to plastics and/or dyes are usually used as decoloring agents.
  • the colored polar polymer material layer obtained according to example 1 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 700 ml water and a polar solvent of 300 ml ethanol having a pH of 10 and a temperature of 110 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of poly(amidoamine-co-acrylic acidjcopolymer in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g of benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor. The remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 2 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml dimethylformamide (DMF) having a pH of 9 and a temperature of 100 °C.
  • the pH 9 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of poly(amidoamine-co-acrylic acid)copolymer in form of particles having a mean particle size diameter of 1 mm to 2 mm was added to the polar solvent.
  • the reaction mixture was stirred at 110 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 3 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 650 ml water and a polar solvent of 350 ml ethanol having a pH of 12 and a temperature of 110 °C.
  • the pH 12 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of poly(amidoamine-co-acrylic acidjcopolymer in form of particles having a mean particle size diameter of 1 mm to 2 mm and 6 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 110 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 99/-1/0; RGB: 250/254/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 4 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml dimethylformamide (DMF) having a pH of 12 and a temperature of 120 °C.
  • the pH 12 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 4 g of poly(amidoamine-co-acrylic acidjcopolymer in form of particles having a mean particle size diameter of 1 mm to 2 mm was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 60 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish - CIELab: 98/-4A2; RGB: 240/254/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 5 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 600 ml water and a polar solvent of 400 ml ethanol having a pH of 9 and a temperature of 120 °C.
  • the pH 9 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of poly(acrylamide-co-sodium methacrylate) hydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm and 7 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 6 is shred to parts having a mean diameter of 3 mm to 5 mm. 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml dimethylformamide (DMF) having a pH of 5 and a temperature of 110 °C. The pH 5 of the polar solvent was adjusted by adding acidic acid before the shred parts are added to the polar solvent. 3 g of
  • poly(acrylamide-co-sodium methacrylatejhydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm was added to the polar solvent.
  • the reaction mixture was stirred at 110 °C and under the pressure built up in the closed pressure reactor during the reaction time of 15 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 7 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml Ethanol having a pH of 8 and a temperature of 120 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 2 g of poly(acrylamide-co- sodium methacrylatejhydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm and 8 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 8 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • dimethylformamide having a pH of 10 and a temperature of 110 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 3 g of poly(acrylamide-co-sodium methacrylatejhydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm was added to the polar solvent.
  • the reaction mixture was stirred at 110 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly reddish shimmering - CIELab: 91/11/5; RGB: 255/223/221.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 9 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 750 ml water and a polar solvent of 250 ml Ethanol having a pH of 10 and a temperature of 100 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of poly(acrylamide- co-sodium methacrylatejhydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm and 7 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor. The remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt- % of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 10 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml dimethylsulfoxide (DMSO) having a pH of 11 and a temperature of 100 °C.
  • DMSO dimethylsulfoxide
  • the pH 11 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 3 g of poly(acrylamide-co-sodium methacrylatejhydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor. The remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 11 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml Ethanol having a pH of 10 and a temperature of 120 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • Poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine in form of particles having a mean particle size diameter of 1 mm to 2 mm and 6 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 80/1/-20; RGB: 180/199/235.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 12 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 750 ml water and a polar solvent of 250 ml Ethanol having a pH of 10 and a temperature of 120 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 6 g of Poly(N,N- dimethylacrylamide-co-sodium acrylate) hydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 90/1/-30; RGB: 211/227/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 13 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 850 ml water and a polar solvent of 150 ml
  • Dimethylformamide (DMF) having a pH of 8 and a temperature of 120 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 4 g of Poly (amidoamine-co-acrylic acid) copolymer in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 60 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 93/3A45; RGB:
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before
  • the colored polar polymer material layer obtained according to example 14 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 650 ml water and a polar solvent of 350 ml Ethanol having a pH of 10 and a temperature of 120 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • Poly(acrylamide-co-sodium methacrylate) hydrogels in form of particles having a mean particle size diameter of 1 mm to 2 mm and 3 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 85/1/-50; RGB: 186/214/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • Example 42
  • the colored polar polymer material layer obtained according to example 15 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml Ethanol having a pH of 9 and a temperature of 110 °C.
  • the pH 9 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of Poly (amidoamine-co-acrylic acid) copolymer in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 110 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly yellowish shimmering - CIELab: 95A4/23; RGB: 251/241/196.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 16 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 850 ml water and a polar solvent of 150 ml Ethanol having a pH of 12 and a temperature of 90 °C.
  • the pH 12 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3 g of Poly(acrylamide-co- sodium methacrylate) hydrogels in form of particles having a mean particle size diameter of 1 mm to 2 mm and 6 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 90°C and under the pressure built up in the closed pressure reactor during the reaction time of 30 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt- % of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • Example 44 The colored polar polymer material layer obtained according to example 17 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml Ethanol having a pH of 11 and a temperature of 100 °C. The pH 11 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent. As decoloring agent 4 g
  • Poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine in form of particles having a mean particle size diameter of 1 mm to 2 mm and 4 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly reddish shimmering - CIELab: 85/35/7; RGB: 255/187/201.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 18 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • Dimethylformamide (DMF) having a pH of 8 and a temperature of 120 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 5 g of Poly (amidoamine-co-acrylic acid) copolymer in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 60 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly reddish shimmering - CIELab: 90/8/0; RGB:
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before
  • Example 46 The colored polar polymer material layer obtained according to example 19 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 650 ml water and a polar solvent of 350 ml Ethanol having a pH of 9 and a temperature of 120°C. The pH 9 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 4 g Poly(acrylamide- co-sodium methacrylate) hydrogels in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 83/1/-15; RGB: 194/207/235.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 20 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 600 ml water and a polar solvent of 400 ml Ethanol having a pH of 10 and a temperature of 120 °C.
  • the pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 5 g of Poly(acrylamide- co-sodium methacrylate) hydrogels in form of particles having a mean particle size diameter of 1 mm to 2 mm and 4 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120°C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is bluish shimmering - CIELab: 73/1/-15; RGB: 166/180/206.
  • the remaining dye in the decolorized shredded polar polymer material was less than 10 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before
  • Example 48 The colored polar polymer material layer obtained according to example 21 is shred to parts having a mean diameter of 3 mm to 5 mm. 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml Ethanol having a pH of 11 and a temperature of 110°C. The pH 11 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent. As decoloring agent 3g of Poly(N,N- dimethylacrylamide-co-sodium acrylate) hydrogel in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g benzyl benzoate was added to the polar solvent. The reaction mixture was stirred at 110°C and under the pressure built up in the closed pressure reactor during the reaction time of 40 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 22 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • Dimethylformamide (DMF) having a pH of 8 and a temperature of 90 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 3 g of Poly(N,N-dimethylacrylamide-co-sodium acrylate) hydrogel in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 90 °C and under the pressure built up in the closed pressure reactor during the reaction time of 40 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt- % of the dye of the colored polymer material before decolorization and colorless for the human eye.
  • the colored polar polymer material layer obtained according to example 23 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • Dimethylformamide having a pH of 8 and a temperature of 100 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 5 g of Poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 50 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly orange shimmering - CIELab: 95/10/15; RGB: 255/233/212.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 24 is shred to parts having a mean diameter of 3 mm to 5 mm. 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 650 ml water and a polar solvent of 350 ml Ethanol having a pH of 10 and a temperature of 120 °C. The pH 10 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 5 g of Poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine in form of particles having a mean particle size diameter of 1 mm to 2 mm and 8 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120°C and under the pressure built up in the closed pressure reactor during the reaction time of 50 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly pink shimmering - CIELab: 85/12/5; RGB: 239/204/203.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 25 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • Dimethylformamide (DMF) having a pH of 8 and a temperature of 100 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 5 g of Poly (amidoamine-co-acrylic acid) copolymer in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 60 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 90/1/-13; RGB:
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before
  • the colored polar polymer material layer obtained according to example 26 is shred to parts having a mean diameter of 3 mm to 5 mm.
  • 1 Og of shred parts are placed in a pressure reactor containing polar solvent of 650 ml water and a polar solvent of 350 ml Ethanol having a pH of 11 and a temperature of 120 °C.
  • the pH 11 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • decoloring agent 3g of Poly(acrylamide- co-sodium methacrylate) hydrogels in form of particles having a mean particle size diameter of 1 mm to 2 mm and 5 g benzyl benzoate was added to the polar solvent.
  • the reaction mixture was stirred at 120°C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 85/-2A65; RGB: 178/216/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the colored polar polymer material layer obtained according to example 27 is shred to parts having a mean diameter of 3 mm to 5 mm. lOg of shred parts are placed in a pressure reactor containing polar solvent of 800 ml water and a polar solvent of 200 ml
  • Dimethylformamide having a pH of 8 and a temperature of 100 °C.
  • the pH 8 of the polar solvent was adjusted by adding NaOH before the shred parts are added to the polar solvent.
  • 4 g of Poly(glycidyl methacrylate) grafted sulfonamide based polystyrene resin with tertiary amine in form of particles having a mean particle size diameter of 1 mm to 2 was added to the polar solvent.
  • the reaction mixture was stirred at 100 °C and under the pressure built up in the closed pressure reactor during the reaction time of 45 minutes. Thereafter the pressure inside the reactor was reduced to atmospheric pressure and the shredded polar polymer material was removed from the reactor.
  • the shredded polar polymer material after decolorization is slightly bluish shimmering - CIELab: 95/0/-55; RGB: 232/241/255.
  • the remaining dye in the decolorized shredded polar polymer material was less than 5 wt.-%, based on 100 wt.-% of the dye of the colored polymer material before decolorization.
  • the polar solvent comprises and/or is exposed to at least one polar decoloring agent for desorption of the coloring agent and absorbing and/or adsorbing the color from the colored synthetic and/or non-synthetic polar-polymer material;
  • the colored synthetic and/or non-synthetic polar-polymer material to be decolorized comprises:
  • At least one organic aromatic coloring agent having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol, wherein the organic aromatic coloring agent is not a chemical reactive organic aromatic coloring agent that forms a chemical covalently bound; i) at least one synthetic and/or non-synthetic polar-polymer having a Mw of about > 1000 g/mol, or
  • synthetic and/or non-synthetic non-polar-polymer comprises in addition: - at least one synthetic and/or non-synthetic polar-polymer having a Mw of about > 1000 g/mol, and/or
  • the polar-additive is selected different to the organic aromatic coloring agent having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol.
  • the polar decoloring agent when added to the decolorization process may be colorless, that means white, transulcent white like frosted glass or transparent
  • the colored synthetic and/or non-synthetic polar-polymer material is decolorized by exposing the colored synthetic and/or non-synthetic polar-polymer material to the polar solvent at a temperature of about > 30 °C to about ⁇ 200 °C, wherein the temperature of the polar solvent is selected > the glass-transition temperature T g and below the decomposition temperature of the colored synthetic and/or non-synthetic polar- polymer material, preferably the temperature of the polar solvent is selected > T g and ⁇ melting temperature T m of the colored synthetic and/or non-synthetic polar-polymer material. It is noted that e-caprolactan melts at about 68 °C but not the colored synthetic and/or non-synthetic polar- polymer material due to the major content of HDPE.
  • any method for decolorizing before wherein the colored synthetic and/or non-synthetic polar-polymer material is decolorized by exposing the colored synthetic and/or non-synthetic polar-polymer material to the polar solvent for about > 15 seconds to about ⁇ 240 minutes, preferably about > 1 minute to about ⁇ 180 minutes, further preferred for about > 5 minutes to about ⁇ 60 minutes, and also preferred for about > 10 minutes to about ⁇ 20 minutes.
  • the polar solvent is liquid at about 23 °C and comprises at least one polar solvent or a mixture of polar solvents, wherein the polar solvent is a solvent or solvent mixture having a dipole, and is preferably selected from the group comprising water, and/or at least one polar organic solvent; wherein further preferred the polar solvent is a mixture of liquids not forming a homogeneous mixture when added together.
  • the polar organic solvent or polar organic solvent mixture is selected from the group Ci to Ce - alcohol, preferably Ethanol and isopropanol, glycols such as diethylene glycol and its oligomers, C3 to Ce
  • ketone preferably acetone, C2 to Ce - aldehyde, Ci to C 6 - carboxylic acid and their derivatives such as acid chlorides or acid amides, other polar aromatic solvents liquid at 23 °C, preferably DMSO, DMF, benzylic alcohol, linear or cyclic aliphatic ethers, preferably diethyl ether or tetrahydrofuran, esters such as ethyl acetate, benzyl benzoate, halogenated solvents such as dichloromethane or trichloromethane.
  • the polar organic solvent is adjusted to a pH in the range of about > 2 to about ⁇ 13, preferably about > 4 to about ⁇ 10, about > 6 to about ⁇ 8, or 7 ⁇ 0.5, wherein the pH is adjusted preferably by adding an acid or basic agent.
  • the organic aromatic coloring agent has a molecular weight Mw in the range of > 250 g/mol to ⁇ 550 g/mol, preferably the organic aromatic coloring agent has a molecular weight Mw in the range of > 270 g/mol to ⁇ 450 g/mol, and more preferably the organic aromatic coloring agent has a molecular weight Mw in the range of > 285 g/mol to ⁇ 400 g/mol.
  • the organic aromatic coloring agent has a solubility in water at 23 °C of ⁇ 0.1 g/1 and > 0 g/1, preferably ⁇ 0.01 g/1 and > 0 g/1, more preferably ⁇ 0.001 g/1 and > 0 g/1.
  • polar decoloring agent selected from the group comprising:
  • polar decoloring agent before used in the decolorization process is preferably free of a dye.
  • polar decoloring agent comprises polar, acidic, and/or basic groups, wherein polar groups for electrostatic interaction are preferred.
  • decoloring agent may have a mean particle size diameter of 0.1 mm to 100 mm, further preferred 1 mm to 50 mm and also preferred 2 mm to 10 mm, more preferred the particles, granulates of the polar decoloring agent may have a round shape, and most preferred the shape of a thin foil, and/or
  • decoloring agent may have a mean particle size diameter of 0.01 mm to 10 mm, further preferred 1 mm to 8 mm and also preferred 2 mm to 5 mm, and more preferred the particles, granulates of the polar decoloring agent may have a round shape, are arranged on or in the surface of a solid substrate, and/or
  • nano- nano-particles having a mean particle size diameter of about > 1 nm to about ⁇ 100 nm, preferably the nano-particles are arranged on the surface of a solid substrate
  • an oxidation process preferably by exposing to at least one oxidation agent select from the group comprising of peroxide, peroxyacetic acid, hydrogen peroxide, ozone, sodium percarbonate, sodium perborate, sodium percarbonate, m-Nitrobenzolsulfonat, H2SO4, HNO3, oxygen-containing anions (oxo anions) of transition metals in high oxidation states such as permanganate MnCV, KMnCE, phosphate, oxygen difluoride fluorine, cryptone difluoride, dichromate CnOv 2 , metal ions such as Ce 4 + , noble metal ions such as those of silver and copper, anions of halo-oxygen acids such bromat BrCE , halogens, such as fluorine, chlorine, bromine and iodine, hypochlorite, sodium hypochlorite, and/or potassium hypochlorite;
  • oxidation agent select from the group comprising of peroxide, peroxyacetic acid
  • a reduction process preferably by exposing to at least one reduction agent select from the group comprising hydrides, H-, NaH, lithium aluminum hydride, sodium hydride, hydrogen sulfide, sodium sulfide, S 2 , Na2S, sulfites, S02 3 , sodium sulfite, sulfurous acid, sulfur dioxide, thiosulphate, sodium dithionite, sodium bisulfite, NaHSCE, formamidine sulfonic acid, sodium hydroxymethanesulfinate also known as rongalite, thiourea dioxide also knwon as thiox, sulfonic acid and its derivatives, borohydride salts, sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium oxide, and mixtures of sodium hydroxide and calcium oxide, sulfinic acid derivatives, borohydrides and/or REDULITE GIN; and/or
  • an oxidation process preferably by exposing to at least one oxidation agent select from the group comprising of peroxide, peroxyacetic acid, hydrogen peroxide, ozone, sodium percarbonate, sodium perborate, sodium percarbonate, m-Nitrobenzolsulfonat, H2SO4, HNO3, oxygen-containing anions (oxo anions) of transition metals in high oxidation states such as permanganate MnCV, KMnCE, phosphate, oxygen difluoride fluorine, cryptone difluoride, dichromate CnOi 2 , metal ions such as Ce 4 + , noble metal ions such as those of silver and copper, anions of halo-oxygen acids such bromat BrCE , halogens, such as fluorine, chlorine, bromine and iodine, hypochlorite, sodium hypochlorite, and/or potassium hypochlorite;
  • oxidation agent select from the group comprising of peroxide, peroxyacetic acid
  • a reduction process preferably by exposing to at least one reduction agent select from the group comprising hydrides, H-, NaH, lithium aluminum hydride, sodium hydride, hydrogen sulfide, sodium sulfide, S 2 , Na2S, sulfites, S02 3 , sodium sulfite, sulfurous acid, sulfur dioxide, thiosulphate, sodium dithionite, sodium bisulfite, NaHSCE, formamidine sulfonic acid, sodium hydroxymethanesulfinate also known as rongalite, thiourea dioxide also knwon as thiox, sulfonic acid and its derivatives, borohydride salts, sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium oxide, and mixtures of sodium hydroxide and calcium oxide, sulfinic acid derivatives, borohydrides and/or REDULITE GIN; and/or
  • the colored synthetic and/or non-synthetic polar-polymer material after decolorization comprises about > 0 wt.-% to about ⁇ 10 wt.-%, preferably about > 0.01 wt.-% to about ⁇ 5 wt.-%, and further preferred about > 0.1 wt.-% to about ⁇ 1 wt.-% of organic aromatic coloring agent having a molecular weight Mw in the range of about > 250 g/mol to about ⁇ 550 g/mol, wherein the organic aromatic coloring agent is not a chemical reactive organic aromatic coloring agent that forms a chemical covalently bound, based on the total amount of said organic aromatic coloring agent in the colored synthetic and/or non-synthetic polar-polymer material before it is decolorized.
  • the method as mentioned to any method for decolorizing before, wherein the colored synthetic and/or non-synthetic polar-polymer material, before it is decolorized comprises about 0.00001 wt.% to about ⁇ 10 wt.%, preferably about 0.001 wt.% to about ⁇ 5 wt.%, further preferred about 0.01 wt.% to about ⁇ 3 wt.%, also preferred about 0.1 wt.% to about ⁇ 2 wt.%, and in addition preferred about 0.5 wt.% to about ⁇ 1 wt.%, organic aromatic coloring agent, based on the total weight of the colored synthetic and/or non-synthetic polar-polymer material before it is decolorized.
  • the colored synthetic and/or non-synthetic polar-polymer material that is exposed to the polar solvent for decolorization has the form of an article, flakes, particles or granulates.
  • the synthetic and/or non-synthetic polar-polymer comprise at least > 5 wt.-% of heteroatoms, based on the total weight of the synthetic and/or non-synthetic polar-polymer, wherein a heteroatom is any atom excluding C-atoms and H-atoms; and/or
  • the synthetic and/or non-synthetic polar-oligomer comprise at least > 5 wt.-% of heteroatoms, based on the total weight of the synthetic and/or non-synthetic polar-oligomer, wherein a heteroatom is any atom excluding C-atoms and H-atoms; and/or - the synthetic and/or non-synthetic polar additive comprise at least > 5 wt.-% of heteroatoms, based on the total weight of the synthetic and/or non-synthetic polar additive, wherein a heteroatom is any atom excluding C-atoms and H-atoms; and/or
  • the polar decoloring agent comprise at least > 5 wt.-% of heteroatoms, based on the total weight of the polar decoloring agent, wherein a heteroatom is any atom excluding C-atoms and H-atoms.
  • the polar decoloring agent is a synthetic and/or non-synthetic polar-polymer or mixture thereof.
  • the polar decoloring agent is a synthetic and/or non-synthetic polar-additive having a Mw > 70 and ⁇ 600 g/mol
  • the synthetic and/or non-synthetic polar-additive having a Mw > 70 and ⁇ 600 g/mol is selected from the group comprising aliphatic acids CH3-[CH2] n -COOH acids (n > 3), amino acids, carboxylic acid amide, hydroxyl acids, fatty acids, aliphatic or aliphatic/aromatic aldehydes and ketones, esters, pentaerythritol, pentaerythritol ester preferably carboxylic acid ester, benzoic acid esters comprising benzylbenzoat or phenylbenzoat, phenylether, alcohols and polyvalent alcohols, preferably glycerine, amines and/or mixtures thereof; and
  • synthetic and/or non-synthetic polar-additive is selected different to the organic aromatic coloring agent having a molecular weight Mw in the range of > 250 g/mol to ⁇ 550 g/mol and is solid at 23° C and is preferably free of a dye.
  • any method for decolorizing before wherein the polar decoloring agent is added to the colorized polymer material for decolorization in a weight ratio of about 0.1 : 1 to 100: 1, preferably of about 0.5: 1 to 80: 1, further preferred about 1 : 1 to 60: 1, also preferred 2: 1 to 50: 1, in addition preferred of about 2.5: 1 to 25: 1, more preferred of about 3: 1 to 10: 1 and furthermore preferred 3.3: 1 to 5: 1.
  • non-polar- polymer is selected from the group of polyalkylene polymers, polyalkylene copolymers, polyakylene block copolymers;
  • the non-polar-polymer is preferably selected from of polymeric aliphatic or aromatic hydrocarbons, preferably polyalkylene polymers, polyalkylene co- and terpolymer with random or block-structure; and more preferred from polyethylen (PE), polypropylene (PP), polybutene (PB), polystyrene, polyisobutylene, polybutadiene, polyisoprene.
  • the polar decoloring agent and/or the colored synthetic and/or colored non-synthetic polar polymer material are dispersed in the polar solvent.
  • the colored synthetic and/or colored non-synthetic polar polymer material to be decolorized may have the shape of an article that is undestroyed, for example a bottle or container, and/or is destroyed, for example shredded to flakes or dust, wherein the article and the shredded article comprises no fibers.
  • the colored synthetic and/or colored non-synthetic polar polymer material to be decolorized is free of fibers and/or free of polyamide fibers.
  • the method for decolorizing a colored synthetic and/or non-synthetic polar-polymer material may not comprise the step of adding a base to the solution, thereby causing the acid dye and the added base to irreversible form an insoluble salt on the colored synthetic or non-synthetic polar-polymer material to be decolorized.
  • the method for decolorizing a colored synthetic and/or non-synthetic polar-polymer material may not comprise the formation of an irreversible insoluble salt of the dye, also named coloring agent on the colored synthetic or non-synthetic polar- polymer material to be decolorized.
  • the method for decolorizing a colored synthetic and/or non-synthetic polar-polymer material may not comprise that the colored synthetic and/or non synthetic polar-polymer material is dissolved in the polar solvent.
  • connections between components are generally to be understood to be functional connections. They can be implemented as direct links or as indirect links via several other components.
  • the order of presented actions is not mandatory; alternative orders are possible.
  • Actions can be implemented in different ways. They could be implemented in software using program instructions; or they could be implemented in hardware; or they could be implemented making use of a combination of hardware and software. It is to be understood that the described embodiments are examples only, which may be modified and/or supplemented in many ways within the scope of the claims.
  • any feature described for a particular embodiment can be used by itself or in combination with other features in any other embodiment.
  • Each feature that has been described for an embodiment of a particular category can also be used in an equivalent manner in an embodiment of any other category.

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Abstract

La présente invention concerne un procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique comprenant l'étape consistant à : exposer la surface externe du matériau polymère polaire synthétique à une solution aqueuse de coloration dispersée, la solution aqueuse de coloration dispersée comprenant : - au moins un colorant aromatique organique présentant un poids moléculaire Mw se situant dans la plage d'environ ≥ 250 g/mol à environ ≤ 550 g/mol, - au moins un agent de dispersion pour disperser le colorant aromatique organique dans la solution aqueuse et - éventuellement au moins un agent de solubilisation, la solution aqueuse de coloration dispersée à laquelle est exposé le matériau polymère synthétique présentant un pH se situant dans la plage d'environ ≥ 2,5 à < 7 et une température se situant dans la plage d'environ ≥ 30 °C à environ ≤ 150 °C, et l'agent de dispersion étant choisi pour être différent de l'agent de solubilisation. En outre, la présente invention concerne un matériau polymère polaire synthétique coloré, coloré par le procédé ci-dessus et, également, un article comprenant au moins un matériau polymère polaire synthétique coloré.
EP20740349.4A 2019-07-24 2020-07-21 Procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique ; matériau polymère polaire synthétique coloré et article associé Pending EP4004093A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP19188085.5A EP3770318A1 (fr) 2019-07-24 2019-07-24 Procédé deteinture réversible et sélective d'un matériau polymère polaire synthétique
EP19188098.8A EP3770208B1 (fr) 2019-07-24 2019-07-24 Procédé de décoloration d'un matériau polymère polaire synthétique ou non synthétique coloré
PCT/EP2020/070573 WO2021013842A1 (fr) 2019-07-24 2020-07-21 Procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique ; matériau polymère polaire synthétique coloré et article associé

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EP20740349.4A Pending EP4004093A1 (fr) 2019-07-24 2020-07-21 Procédé de coloration réversible et sélective d'un matériau polymère polaire synthétique ; matériau polymère polaire synthétique coloré et article associé

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WO2022190131A1 (fr) * 2021-03-11 2022-09-15 Kannappan Kiruthika Composition de démontage de couleur pour textiles en coton teints et procédé associé
EP4163325A1 (fr) * 2021-10-07 2023-04-12 Smart Coloring GmbH Procédé de décoloration d'un article en plastique coloré doté d'une couche extérieure
NL2032034B1 (en) * 2022-05-31 2023-12-12 Orange Dynamics B V Method for colouring a polymeric film and coloured polymeric film

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