WO2025003531A1 - Composants pour l'électromobilité - Google Patents

Composants pour l'électromobilité Download PDF

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Publication number
WO2025003531A1
WO2025003531A1 PCT/EP2024/074456 EP2024074456W WO2025003531A1 WO 2025003531 A1 WO2025003531 A1 WO 2025003531A1 EP 2024074456 W EP2024074456 W EP 2024074456W WO 2025003531 A1 WO2025003531 A1 WO 2025003531A1
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Prior art keywords
parts
mass
phthaloperin
oxybis
polyester
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PCT/EP2024/074456
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German (de)
English (en)
Inventor
Lars MAY
Joerg-Dietrich Jentsch
Marvin KISCHKEWITZ
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Lanxess Deutschland GmbH
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Lanxess Deutschland GmbH
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Publication of WO2025003531A1 publication Critical patent/WO2025003531A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • C08K5/3465—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • 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
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • the present invention relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number starting with "2" in the RAL color table containing polymer compositions based on at least one polyester and a colorant with an average particle size d50 to be determined according to ISO 13320 by means of laser diffractometry in the range from 1 to 12 pm containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, and the use of a colorant with an average particle size d50 to be determined according to ISO 13320 in the range from 1 to 12 pm containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of
  • thermoplastics such as polyester are an important material due to their good mechanical stability, chemical resistance, very good electrical properties and good processability, especially in the area of components for motor vehicles. They have therefore been an important component in the manufacture of sophisticated motor vehicle components for many years. While the combustion engine was the dominant drive concept for many years, the search for alternative drive concepts has also given rise to new requirements with regard to the choice of materials. Electromobility plays a key role here, with key components for the electric drive of vehicles being marked orange, so-called electromobility components in the sense of the present invention.
  • Electromobility components are known to the person skilled in the art from EP 3 947 020 B1, in which they can be, for example, distribution boxes, control units and/or wiring, marked as (172). Electromobility components can be components that are in direct contact with live parts, as well as those that have the function of contact protection, warning marking or shielding in the immediate vicinity or spatial proximity to them, whereby components that are in direct contact with the live parts are preferred according to the invention.
  • electromobility components are preferably standard or round cell modules, cell housings, cell connectors, cell contact systems, module connectors, pressure compensation elements, seals and intelligent battery management systems.
  • electromobility components are preferably modules or stack modules, metallic bipolar plates, end and media modules and sealing systems.
  • electromobility components can be seals and other components, in particular functionally integrated housing covers, housing seals, shaft seals, plate carriers and punched packages.
  • electromobility components in the sense of the present invention also include shielding systems and dynamic precision parts.
  • Examples include machine-related sources of error on the mixing screw, mixing cylinder that is too small, defective color dosing, material hopper that is too large or an electrostatic charge on the color or colorant.
  • Material-related sources of error can be the incompatibility of the masterbatch or colorant with the plastic to be processed, insufficient solubility of the colorant in the plastic to be processed, thermal sensitivity of the colorant, too large granules or too high a pigment content.
  • Methodological sources of error can be too low back pressure during injection molding, too high screw speed, too high or too low melt temperature, too high or too low injection speed, too high or too low mold temperature, or insufficient or too high color dosage.
  • tool-related sources of error can also encourage the occurrence of color streaks, such as flow cross-sections that are too small, flow paths that are too long, unfavorable positions of weld lines or sections on the injection molded product that are too small for injection molding.
  • streak-reduced or streak-free processing of orange polyester-based Moulding compounds, especially in injection moulding present a particular challenge for the specialist.
  • the object of the present invention was therefore to provide electromobility components based on polyesters which, on the one hand, are characterized by the color orange, but at the same time are as free as possible from color streaks and finally show an improved (color) brilliance compared to the state of the art according to DIN EN ISO 11664-4, whereby orange polyester-based electromobility components based on alternative dyes and/or alternative physical properties of these orange dyes are to be considered as the state of the art.
  • Color brilliance is a general term for colorants, which - based on the physical term and also referred to as brilliance in the context of the present application - non-specifically describes the light effect of a body color. It is generally dependent on the color saturation, the luminance, but also on the directed light of point-shaped light sources (brilliance of wave theory), which creates gloss on shiny surfaces or transparent materials through reflection of the light source or refraction of the light.
  • (color) brilliance according to DIN EN ISO 11664-4, samples are subjected to a coloristic measurement within the scope of the present invention. For this purpose, polyester granulate colored with 1 wt.% titanium dioxide is dried in a circulating air dryer at 120°C for 4 hours.
  • 1 kg of the granulate is mixed with 0.20 wt.% of the colorant to be examined and this mixture is extruded at a melt temperature of 280°C using a twin-screw extruder and then granulated again.
  • the colored granulate is dried at 120°C for 4 hours and sample plates measuring 4cm x 6cm x 0.2cm are produced from the dried, colored granulate on an injection molding machine at a melt temperature of 280°C, a dynamic pressure of 10 bar and a mold temperature of 80°C. After at least ten injection cycles, sample plates are removed for color measurement and left to rest at room temperature for at least 1 hour. The reflectance measurements are then carried out on the sample plates using a d/8° spectrophotometer.
  • the colorant containing the isomers 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 is used with an average particle size d50 in the range of 1 to 12 pm, determined using ISO 13320.
  • an average particle size d50 in the range of 1 to 12 pm, determined using ISO 13320.
  • the d50 of a particle size distribution refers to the particle size that corresponds to the cumulative frequency of 50%.
  • the d50 is a typical parameter for assessing powder quality.
  • the d50 value of a sample after volume distribution is 5 pm
  • the d50 is referred to in mathematical statistics as what is commonly called the median.
  • the invention relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" containing polymer compositions based on at least one polyester and a colorant with an average particle size d50 to be determined by laser diffractometry according to ISO 13320 in the range from 1 to 12 pm containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, wherein in the polymer compositions 0.01 to 5 parts by mass of colorant are present per 100 parts by mass of polyester. present.
  • the invention preferably relates to electromobility components with a color difference AE ⁇ 10 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" containing polymer compositions based on at least one polyester and a colorant with an average particle size d50 to be determined by laser diffractometry according to ISO 13320 in the range from 1 to 12 pm containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, wherein in the polymer compositions 0.01 to 5 parts by mass of colorant are used per 100 parts by mass of polyester. present.
  • the invention particularly preferably relates to electromobility components with a color difference AE ⁇ 5 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" containing polymer compositions based on at least one polyester and a colorant with an average particle size d50 to be determined by laser diffractometry according to ISO 13320 in the range from 1 to 12 pm containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, wherein in the polymer compositions 0.01 to 5 parts by mass of colorant are used per 100 parts by mass of polyester. present.
  • Preferred electromobility components are those in which, based on the polymer compositions, 0.01 to 3 parts by mass of colorant containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-
  • the invention also relates to the use of a colorant containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined by means of laser diffractometry in accordance with ISO 13320 in polymer compositions for obtaining color streak-reduced polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number of the RAL color table beginning with "2", where in the polymer compositions contain 0.01 to 5 parts by mass of colorant per 100 parts by mass of at least one polyester.
  • Reduced color streaks in the sense of the present invention means a reduction of superficially visible color streaks on samples after injection molding by at least 10% compared to a colorant based on 10,10'-oxybis-12H-phthaloperin-12-one obtainable according to Example 3 in EP 1 118 640 A1.
  • the invention preferably relates to the use of a colorant containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined by laser diffractometry according to ISO 13320 in polymer compositions for obtaining color streak-reduced polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number starting with "2" in the RAL color table and a color number according to DIN EN ISO 11664-4 to be determined (color) brilliance with an AC* > 1 to a corresponding comparison sample whose isomer ratio is not in the range of 1:1:0.8-1.5 to 1:1.5:0.8-1.5,
  • the invention particularly preferably relates to the use of a colorant containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8 -1 ,5 to 1 : 1 ,5 : 0.8 - 1 ,5 with an average particle size d50 to be determined according to ISO 13320 by means of laser diffractometry in the range of 1 to 12 pm in polymer compositions for obtaining color streak-free electromobility components based at least on polyester with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number starting with "2" in the RAL color table and a (color) brilliance to be determined according to DIN EN ISO 11664-4 with an AC* > 1 to a corresponding comparison sample whose isomer ratio is not in the range
  • Free of color streaks in the sense of the present invention means a reduction of superficially visible color streaks on polyester-based samples after injection molding by at least 50%, for example in comparison to a colorant based on 10,10'-oxybis-12H-phthaloperin-12-one obtainable according to Example 3 in EP 1 118 640 A1.
  • the invention particularly preferably relates to the use of a colorant containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined according to ISO 13320 by means of laser diffractometry in polymer compositions for obtaining color streak-free electromobility components based at least on polyester with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number starting with "2" in the RAL color table and a (colour) brilliance to be determined according to DIN EN ISO 11664-4 with an AC* > 1 to a corresponding comparison sample whose isomer ratio is not in the range of 1 : 1 : 0.8 -1 .
  • the preparation of polymer compositions for the production of electromobility components according to the invention is carried out by means of compounding and subsequent Processing by injection molding, extrusion or blow molding by mixing the at least one polyester to be used as starting material with the colorant containing the isomer mixture 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm, determined by laser diffractometry in accordance with ISO 13320, in at least one mixing tool in the ratio given above.
  • the electromobility components according to the present invention are preferably injection molded, extrusion or blow molded components, preferably injection molded components.
  • Electromobility components according to the invention for electromobility are colored orange by the colorant containing the isomer mixture 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range of 1 to 12 pm to be determined by means of laser diffractometry in accordance with ISO 13320, with color tones that are in the RAL color system of the color number RAL2001, RAL2003, RAL2004, RAL2007, RAL2008, RAL2009, RAL2010 and RAL2011 are particularly preferred and the colours which correspond to the colour number RAL2003, RAL2008, RAL 2010 and RAL2011 in the RAL colour system are very particularly preferred.
  • Similar colors that are permissible according to the invention and are included in the present invention are those whose color difference in the L*a*b* system has an AE of ⁇ 20, preferably an AE ⁇ 10, particularly preferably AE ⁇ 5 to a color number in the RAL color table that begins with "2".
  • AE defined in EN ISO 11664-4, see, for example, https://de.wikipedia.org/wiki/Delta_E.
  • orange is a color that has a color number in the RAL color system according to https://de.wikipedia.Org/wiki/RAL-Farbe#Orange in the RAL color table that begins with a "2".
  • Table 1 a distinction is made between orange tones as of the filing date of the present invention according to Table 1:
  • Tab.1 shows the device-independent CIE L*a*b* color values for the respective RAL value: L* stands for the luminance, a* describes the color location with respect to the red-green axis and b* describes the color location with respect to the yellow-blue axis using D65 standard light with a 10° field of view of a standard observer.
  • the color model is standardized in EN ISO 11664-4 "Colorimetry -- Part 4: CIE 1976 L*a*b* Color space”.
  • For L*a*b* color space also: CIELAB
  • Each color in the color space is defined by a color location with the Cartesian coordinates ⁇ L*, a*, b* ⁇ .
  • the a* axis describes the green or red component of a color, with negative values for green and positive values stand for red.
  • the b* axis describes the blue or yellow component of a color, with negative values representing blue and positive values representing yellow.
  • the a* values range from approximately -170 to +100, the b* values from -100 to +150, with the maximum values only being reached at medium brightness of certain colors.
  • the CIELAB color solid has its greatest extent in the medium brightness range, but this varies in height and size depending on the color range.
  • the invention relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" based on polymer compositions containing, in addition to at least one polyester and the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one to be used as colorant in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, at least one filler and/or reinforcing material, preferably in the range of 1 to 150 parts by mass, particularly preferably in the range of 5 to 80 parts by mass, very particularly preferably in the range of 10 to 50 parts by mass, in each case based on 100 parts by mass of polyester.
  • the invention relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" based on polymer compositions containing, in addition to the at least one polyester and the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one to be used as colorant in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, at least one flame retardant, preferably in an amount of 3 to 100 parts by mass, particularly preferably in an amount of 5 to 80 parts by mass, very particularly preferably in an amount of 10 to 50 parts by mass, in each case based on 100 Mass fraction of polyester.
  • the invention relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" based on polymer compositions containing, in addition to the at least one polyester and the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one to be used as colorant in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, at least one additive, preferably 0.01 to 80 parts by mass, particularly preferably 0.05 to 50 parts by mass, completely particularly preferably 0.1 to 30 parts by mass, each based on 100 parts by mass of polyester.
  • C2-C10-polyalkylene terephthalates which are preferably used as polyesters in the context of the present invention are reaction products of an alcohol moiety with 2 to 10 C atoms in the alcohol moiety and terephthalic acid.
  • C2-C10-polyalkylene terephthalates are known to the person skilled in the art and are adequately described in the literature. They contain an aromatic ring in the main chain which originates from terephthalic acid and an aliphatic moiety which originates from a dihydroxy compound. The aromatic ring of terephthalic acid can also be substituted.
  • Preferred substituents are halogens or C1-C4-alkyl groups. Preferred halogens are chlorine or bromine.
  • Preferred C1-C4-alkyl groups are methyl, ethyl, n-propyl or n-, i- or t-butyl groups.
  • C2-C polyalkylene terephthalates can be prepared by reacting aromatic dicarboxylic acids, their esters or other ester-forming derivatives with aliphatic dihydroxy compounds in a manner known to the person skilled in the art.
  • a portion of the terephthalic acid used to prepare them can be replaced by up to 30 mol% of 2,6-naphthalenedicarboxylic acid or isophthalic acid or mixtures thereof.
  • Up to 70 mol%, preferably not more than 10 mol%, of the terephthalic acid can be replaced by aliphatic or cycloaliphatic dicarboxylic acids such as adipic acid, azelaic acid, sebacic acid, dodecanedioic acids or cyclohexanedicarboxylic acids.
  • diols with 2 to 6 carbon atoms in particular 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,4-hexanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, neopentyl glycol, or mixtures thereof are preferred.
  • Particularly preferred polyalkylene terephthalates are derived from alkanediols with 2 to 4 carbon atoms.
  • PET polyethylene terephthalate
  • PBT polypropylene terephthalate
  • PET and/or PBT which contain up to 1% by weight, preferably up to 0.75% by weight, of 1,6-hexanediol and/or 2-methyl-1,5-pentanediol as further monomer units.
  • C2-C10 polyalkylene terephthalates to be used as polyesters according to the invention have a viscosity number to be determined according to ISO 1628 in the range from 50 to 220, preferably in the range from 80 to 160, measured in a 0.5 wt.% solution in a phenol/o-dichlorobenzene mixture, weight ratio 1:1 at 25°C.
  • C2-C10-polyalkylene terephthalates preferably used as polyesters according to the invention preferably have a carboxyl end group content of up to 100 meq/kg polyester, particularly preferably a carboxyl end group content of up to 50 meq/kg polyester and especially preferably a carboxyl end group content of up to 40 meq/kg polyester.
  • Such C2-C polyalkylene terephthalates can be prepared, for example, by the process of DE-A 4401 055.
  • the carboxyl end group content is usually determined by titration methods, in particular potentiometry.
  • Particularly preferred C2-C polyalkylene terephthalates to be used as polyesters are produced using Ti catalysts. After polymerization, these preferably have a residual Ti content of ⁇ 250 ppm, particularly preferably ⁇ 200 ppm, very particularly preferably ⁇ 150 ppm.
  • the polybutylene terephthalate (PBT) [CAS No. 24968-12-5] which is preferably used according to the invention as C2-C polyalkylene terephthalate is prepared from terephthalic acid or its reactive derivatives and butanediol by known methods (Kunststoff-Handbuch, Vol. VIII, pp. 695-743, Karl Hanser Verlag, Kunststoff 1973).
  • the PBT to be used as polyester contains at least 80 mol%, preferably at least 90 mol%, based on the dicarboxylic acid,
  • PBT which is preferably used as polyester according to the invention, can be used in a
  • Embodiment containing, in addition to terephthalic acid residues, up to 20 mol% of residues of other aromatic dicarboxylic acids having 8 to 14 C atoms or residues of aliphatic dicarboxylic acids having 4 to 12 C atoms, in particular residues of phthalic acid, isophthalic acid, naphthalene-2,6-dicarboxylic acid, 4,4'-diphenyldicarboxylic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, cyclohexanediacetic acid, cyclohexanedicarboxylic acid, 2,5-furandicarboxylic acid.
  • phthalic acid isophthalic acid, naphthalene-2,6-dicarboxylic acid, 4,4'-diphenyldicarboxylic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, cyclohexanediacetic acid,
  • PBT to be used as polyester according to the invention can, in one embodiment, contain, in addition to butanediol, up to 20 mol% of other aliphatic diols having 3 to 12 C atoms or up to 20 mol% of cycloaliphatic diols having 6 to 21 C atoms, preferably residues of 1,3-propanediol, 2-ethyl-1,3-propanediol, neopentyl glycol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, 3-methyl-2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 2,2,4-trimethyl-1,5-pentanediol, 2- Ethylhexanediol-1,3, 2,2-diethylpropaned
  • PBT which is preferably used as a polyester, has an intrinsic viscosity according to EN-ISO 1628/5 in the range from 40 to 170 cm 3 /g, particularly preferably in the range from 50 to 150 cm 3 /g, very particularly preferably in the range from 65 to 135 cm 3 /g, each measured in the Ubbelohde viscometer in phenol/o-dichlorobenzene (1:1 parts by weight) at 25°C.
  • the intrinsic viscosity /V also known as the Staudinger index or intrinsic viscosity, is proportional to the average molecular mass according to the Mark-Houwink equation and is the extrapolation of the viscosity number VN for the case of vanishing polymer concentrations.
  • the VN [ml/g] is obtained by measuring the solution viscosity in a capillary viscometer, for example an Ubbelohde viscometer.
  • the solution viscosity is a measure of the average molecular weight of a plastic. It is determined on the dissolved polymer, using different solvents (m-cresol, tetrachloroethane, phenol, 1,2-dichlorobenzene, etc.) and concentrations.
  • the viscosity number VN makes it possible to monitor the processing and usage properties of plastics. Thermal stress on the polymer, aging processes or the effects of chemicals, weathering and light can be investigated using comparative measurements. See also: http://de.wikipedia.org/wiki/Viskosimetrie and http://de.wikipedia.org/wiki/Mark-Houwink-Gleichung.
  • PBT which is preferably used as a polyester
  • PBT blends used according to the invention are produced by compounding.
  • conventional additives in particular mold release agents or elastomers, can also be mixed into the melt, thereby improving the properties of the blends.
  • PBT to be used preferably according to the invention can be obtained as Pocan® B 1300 from Lanxess GmbH, Cologne.
  • thermoplastic from the group of polycarbonates can also be used as polyester.
  • Polycarbonates to be used preferably according to the invention are those homopolycarbonates or copolycarbonates based on bisphenols of the general formula (I),
  • Z is a divalent organic radical having 6 to 30 C atoms which contains one or more aromatic groups.
  • At least one polycarbonate based on bisphenols of the formula (la) is used as polyester wherein
  • A represents a single bond or a radical from the series Ci-Cs-alkylene, C2-C5-alkylidene, Cs-Ce-cycloalkylidene, -O-, -SO-, -CO-, -S-, -SO2-, C6-Ci2-arylene, to which further aromatic rings, optionally containing heteroatoms, can be condensed, or A represents a radical of the formula (II) or (III)
  • R 7 and R 8 can be selected individually for each Y and independently of one another represent hydrogen or Ci-Ce-alkyl, preferably hydrogen, methyl or ethyl,
  • B is each Ci-Ci2-alkyl, preferably methyl, halogen, preferably chlorine and/or bromine, x is each independently 0, 1 or 2, p is 1 or 0,
  • Y represents carbon
  • m represents an integer from 4 to 7, preferably 4 or 5, with the proviso that on at least one Y (carbon atom) R 7 and R 8 simultaneously represent alkyl.
  • Y is -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -; when m is 5, Y is -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -; when m is 6, Y is -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -; and when m is 7, Y is -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -CR 7 R 8 -.
  • Preferred bisphenols containing the general formula (II) are bisphenols from the group dihydroxydiphenyls, bis-(hydroxyphenyl)-alkanes, bis-(hydroxyphenyl)-cycloalkanes, indanebisphenols, bis-(hydroxyphenyl)-sulfides, bis-(hydroxyphenyl)-ethers, bis-(hydroxyphenyl)-ketones, bis-(hydroxyphenyl)-sulfones, bis-(hydroxyphenyl)-sulfoxides and a,a'-bis-(hydroxyphenyl)-diisopropylbenzenes.
  • Also derivatives of the bisphenols mentioned which are preferably obtainable by alkylation or halogenation on the aromatic rings of the bisphenols mentioned, are preferably used bisphenols containing the general formula (II).
  • Particularly preferred bisphenols containing the general formula (II) are hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis-(4-hydroxyphenyl) sulfide, bis-(4-hydroxyphenyl) sulfone, bis-(3,5-dimethyl-4 -hydroxyphenyl)-methane, bis-(3,5-dimethyl-4-hydroxyphenyl)-sulfone, 1 ,1-Bis-(3,5-dimethyl-4-hydroxyphenyl)-p/m-diisopropylbenzene, 1,1-Bis-(4-hydroxyphenyl)-1-phenyl-ethane, 1,1-Bis-(3, 5-dimethyl-4-hydroxyphenyl)-cyclohexane, 1,1-bis-(4-hydroxyphenyl)-3-methylcyclohexane, 1 ,1-Bis-(4-hydroxyphenyl)-3,3-dimethylcyclohe
  • bisphenol A 2,2-bis-(3-chloro-4-hydroxyphenyl)-propane, 2,2-bis-(3,5-dibromo- 4-hydroxyphenyl)- propane, 2,4-bis-(4-hydroxyphenyl)-2-methylbutane, 2,4-bis-(3,5-dimethyl-4-hydroxyphenyl)- 2-methylbutane, a,a'-Bis-(4-hydroxyphenyl)-o-diisopropylbenzene, a,a'-Bis-(4-hydroxy-phenyl)-m-diisopropylbenzene (ie bisphenol M), a,a'-Bis-(4 -hydroxyphenyl)-p-diiso-propylbenzene and indane bisphenol.
  • the polycarbonates used as polyesters can also be produced using known processes.
  • Preferred processes for producing polycarbonates are, for example, production from bisphenols with phosgene using the interfacial process, or from bisphenols with phosgene using the homogeneous phase process, the so-called pyridine process, or from bisphenols with carbonic acid esters using the melt transesterification process.
  • the bisphenols mentioned and processes for their preparation are described, for example, in the monograph H. Schnell, "Chemistry and Physics of Polycarbonates", Polymer Reviews, Volume 9, pp.
  • Indanebisphenols and their preparation are described, for example, in US-A 3 288 864, in JP-A 60 035 150 and in US-A 4 334 106.
  • Indanebisphenols can be prepared, for example, from isopropenylphenol or its derivatives or from dimers of isopropenylphenol or its derivatives in the presence of a Friedel-Craft catalyst in organic solvents.
  • melt transesterification process is described in H. Schnell, "Chemistry and Physics of Polycarbonates", Polymer Reviews, Volume 9, pp. 44 to 51, Interscience Publishers, New York, London, Sidney, 1964 and in DE-A 1 031 512.
  • raw materials and auxiliary materials with a low level of impurities are preferably used.
  • the bisphenols and carbonic acid derivatives used should be as free as possible from alkali ions and alkaline earth ions.
  • Raw materials of this kind can be obtained, for example, by recrystallizing, washing or distilling the carbonic acid derivatives, in particular carbonic acid esters, and the bisphenols.
  • Polycarbonates to be used as polyesters according to the invention preferably have a weight average molar mass M w in the range from 10,000 to 200,000 g/mol, which can be determined by ultracentrifugation (see K. Schilling, Analytical Ultracentrifugation, Nanolytics GmbH, Dallgow, pages 1-15) or scattered light measurement in accordance with DIN EN ISO 16014-5:2012-10.
  • the polycarbonates to be used particularly preferably have a weight average molar mass in the range from 12,000 to 80,000 g/mol, particularly preferably a weight average molar mass in the range from 20,000 to 35,000 g/mol.
  • the average molar mass of polycarbonates preferably used as polyesters according to the invention can preferably be adjusted in a known manner by an appropriate amount of chain terminators.
  • the chain terminators can be used individually or as a mixture of different chain terminators.
  • Preferred chain terminators are both monophenols and monocarboxylic acids.
  • Preferred monophenols are phenol, p-chlorophenol, p-tert-butylphenol, cumylphenol or 2,4,6-tribromophenol, and long-chain alkylphenols, in particular 4-(1,1,3,3-tetramethylbutyl)phenol or monoalkylphenols or dialkylphenols with a total of 8 to 20 carbon atoms in the alkyl substituents, in particular 3,5-di-tert-butylphenol, p-tert-octylphenol, p-dodecylphenol, 2-(3,5-dimethylheptyl)phenol or 4-(3,5-dimethylheptyl)phenol.
  • Preferred monocarboxylic acids are benzoic acid, alkylbenzoic acids or halogenbenzoic acids.
  • Particularly preferred chain terminators are phenol, p-tert-butylphenol, 4-(1,1,3,3-tetramethylbutyl)phenol or cumylphenol.
  • the amount of chain terminators to be used is preferably in the range of 0.25 to 10 mol %, based on the sum of the bisphenols used.
  • Polycarbonates preferably used as polyesters according to the invention can be branched in a known manner, preferably by incorporating trifunctional or more than trifunctional branching agents.
  • Preferred branching agents are those with three or more than three phenolic groups or those with three or more than three carboxylic acid groups.
  • branching agents are phloroglucin, 4,6-dimethyl-2,4,6-tri-(4-hydroxyphenyl)-heptene-2, 4,6-dimethyl-2,4,6-tri-(4-hydroxyphenyl).
  • branching agents are 1,1,1-tris-(4-hydroxyphenyl)ethane or 3,3-bis-(3-methyl-4-hydroxyphenyl)-2-oxo-2,3-dihydroindole.
  • the amount of branching agent to be used is preferably in the range of 0.05 mol% to 2 mol%, based on the moles of bisphenols used.
  • the branching agents are preferably initially introduced with the bisphenols and the chain terminators in an aqueous alkaline phase, or are added dissolved in an organic solvent together with the carbonic acid derivatives.
  • the branching agents are preferably added together with the dihydroxyaromatics or bisphenols.
  • Catalysts preferably used in the production of polycarbonates preferably used as polyesters according to the invention by the melt transesterification process are ammonium salts and phosphonium salts, as described, for example, in US-A 3 442 864, JP-A-14742/72, US-A 5 399 659 or DE-A 19 539 290.
  • copolycarbonates can also be used as polyesters.
  • Copolycarbonates in the sense of the invention are in particular polydiorganosiloxane-polycarbonate block copolymers whose weight average molar mass M w is preferably in the range from 10,000 to 200,000 g/mol, particularly preferably in the range from 20,000 to 80,000 g/mol, determined by gel chromatography in accordance with DIN EN ISO 16014-5:2012-10 after prior calibration by light scattering measurement or Ultracentrifugation.
  • the content of aromatic carbonate structural units in the polydiorganosiloxane-polycarbonate block copolymers is preferably in the range from 75 to 97.5% by weight, particularly preferably in the range from 85 to 97% by weight.
  • the content of polydiorganosiloxane structural units in the polydiorganosiloxane-polycarbonate block copolymers is preferably in the range from 25 to 2.5% by weight, particularly preferably in the range from 15 to 3% by weight.
  • the polydiorganosiloxane-polycarbonate block copolymers can preferably be prepared starting from polydiorganosiloxanes containing a,o-bishydroxyaryloxy end groups and having an average degree of polymerization P n in the range from 5 to 100, particularly preferably having an average degree of polymerization P n in the range from 20 to 80.
  • Polycarbonates that are preferred for use as polyesters according to the invention are available, for example, under the brand name Makrolon® from Covestro AG, Leverkusen.
  • the polycarbonates to be used as polyesters can be mixed with conventional additives, in particular mold release agents, in the melt or applied to the surface.
  • Planetary roller extruders or co-kneaders includes the process operations of conveying, melting, dispersing, mixing, degassing and pressure build-up.
  • blends of polycarbonate and polyalkylene terephthalates which are also offered by Covestro AG under the Makroblend® brand, can also be used as polyesters.
  • These are preferably PC-PET blends, PC-PBT blends or PC-PCT-G blends, where PC stands for polycarbonate, PET for polyethylene terephthalate, PBT for polybutylene terephthalate and PCT for polycyclohexylenedimethylene terephthalate.
  • this isomer mixture is obtainable by melting 300 g of phenol at a temperature of 60°C and adding 45 g (285 mmol) of 1,8-diaminonaphthalene and 3.1 g of 2,6-lutidine (28.5 mmol) to it and stirring the mixture for 30 minutes. Then 45 g (145 mmol) of 4,4-oxydiphthalic anhydride are added and the reaction mixture is stirred for a further 30 minutes. The reaction mixture is then heated to 175°C and kept at this temperature for 10 hours, during which the water of reaction formed is distilled off.
  • the present invention therefore also relates to the isomer mixture containing 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5, preferably with a particle size d50 in the range from 1 to 12 pm, to be determined by laser diffractometry according to ISO 13320.
  • the isomer mixture to be used as a colorant can be used directly as a powder, or in the form of a masterbatch, in the form of a compact or in the form of a concentrate, with masterbatches being preferred and masterbatches in a polyester matrix being particularly preferred.
  • At least one filler or reinforcing material is used in the polymer compositions in addition to the polyester and the colorant. Mixtures of two or more different fillers and/or reinforcing materials can also be used.
  • At least one filler or reinforcing material is selected from the group consisting of carbon fibers [CAS No. 7440-44-0], glass beads or solid or hollow glass beads, or glass fibers, or ground glass, amorphous quartz glass, aluminum borosilicate glass with an alkali content of 1% (E-glass) [CAS No. 65997-17-3], amorphous silica [CAS No. 7631-86-9], quartz powder [CAS No. 14808-60-7], calcium silicate [CAS No. 1344-95-2], calcium metasilicate [CAS No. 10101-39-0], magnesium carbonate [CAS No. 546-93-0], kaolin [CAS No. 1332-58-7], calcined kaolin [CAS No.
  • glass fibers and wollastonite are particularly preferred, with glass fibers being particularly preferred.
  • the expert distinguishes between chopped fibers, also known as short fibers, with a length in the range of 0.1 to 1 mm, long fibers with a length in the range of 1 to 50 mm and continuous fibers with a length L > 50 mm.
  • Short fibers are preferably used in injection molding technology and can be processed directly with an extruder.
  • Long fibers can also be processed in extruders. They are used on a large scale in fiber injection molding. Long fibers are often mixed into thermosets as fillers.
  • Continuous fibers are used as rovings or fabrics in fiber-reinforced plastics. Products with continuous fibers achieve the highest stiffness and strength values.
  • Ground glass fibers are also offered, the length of which after grinding is typically in the range of 70 to 200 pm.
  • Glass fibers preferably used as filler or reinforcing material according to the invention are cut long glass fibers with an average initial length determined by means of laser diffraction particle size analysis (laser granulometric measurement or laser diffractometry) in accordance with ISO 13320 in the range from 1 to 50 mm, particularly preferably in the range from 1 to 10 mm, very particularly preferably in the range from 2 to 7 mm.
  • laser diffraction particle size analysis laser granulometric measurement or laser diffractometry
  • the glass fibers in the molding compound or in the product may have a smaller d90 or d50 value than the glass fibers originally used.
  • the arithmetic mean of the glass fiber length after processing is often only in the range of 150 pm to 300 pm, which is why the length, width and diameter information given in this description for fillers and reinforcing materials, in particular for glass fibers, refers to the state before any processing, in particular before compounding or before processing, in particular in injection molding.
  • Preferred glass fibers to be used as fillers or reinforcing materials have an average fiber diameter, determined by laser diffraction according to ISO 13320, in the range of 7 to 18 pm, particularly preferably in the range of 9 to 15 pm.
  • the glass fibers preferably used as fillers or reinforcing materials are provided with a suitable sizing system or an adhesion promoter or adhesion promoter system.
  • a silane-based sizing system or an adhesion promoter is used.
  • At least one flame retardant is used in the polymer compositions in addition to the polyester and the colorant.
  • Preferred flame retardants are mineral flame retardants, nitrogen-containing flame retardants or phosphorus-containing flame retardants.
  • Magnesium hydroxide is particularly preferred among the mineral flame retardants.
  • Magnesium hydroxide [CAS No. 1309-42-8] can be contaminated due to its origin and method of production. Typical impurities are, for example, silicon, iron, calcium and/or aluminum-containing species, which can be embedded in the magnesium hydroxide crystals, for example in the form of oxides.
  • the magnesium hydroxide used as a mineral flame retardant can be uncoated or coated.
  • the magnesium hydroxide used as a mineral flame retardant is preferably coated with coatings based on stearates or aminosiloxanes, particularly preferably with aminosiloxanes.
  • Magnesium hydroxide which is preferably used as a mineral flame retardant, has an average particle size d50, determined by laser diffraction according to ISO 13320, in the range from 0.5 pm to 6 pm, with a d50 in the range from 0.7 pm to 3.8 pm being preferred and a d50 in the range from 1.0 pm to 2.6 pm being particularly preferred.
  • Magnesium hydroxide types suitable according to the invention as mineral flame retardants are, for example, Magnifin® H5IV from Martinswerk GmbH, Bergheim, Germany or Hidromag® Q2015 TC from Penoles, Mexico City, Mexico.
  • Preferred nitrogen-containing flame retardants are the reaction products of trichlorotriazine, piperazine and morpholine according to CAS No. 1078142-02-5, in particular MCA PPM Triazine HF from MCA Technologies GmbH, Biel-Benken, Switzerland, as well as melamine cyanurate and condensation products of melamine, in particular Meiern, Melam, Melon or more highly condensed compounds of this type.
  • Preferred inorganic nitrogen-containing compounds are ammonium salts.
  • salts of aliphatic and aromatic sulfonic acids and mineral flame retardant additives in particular aluminum hydroxide or Ca-Mg carbonate hydrates (DE-A 4 236 122) can also be used.
  • zinc-containing compounds can also be used. These preferably include zinc oxide, zinc borate, zinc stannate, zinc hydroxystannate, zinc sulfide and zinc nitride, or mixtures thereof.
  • Preferred phosphorus-containing flame retardants are organic metal phosphinates, aluminum salts of phosphonic acid, red phosphorus, inorganic metal hypophosphites, metal phosphonates, derivatives of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxides (DOPO derivatives), resorcinol bis(diphenyl phosphate) (RDP) including oligomers, bisphenol A bisdiphenyl phosphate (BDP) including oligomers, melamine pyrophosphate, melamine polyphosphate, melamine poly(aluminum phosphate), melamine poly(zinc phosphate) or phenoxyphosphazene oligomers and mixtures thereof.
  • DOPO derivatives 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxides
  • RDP resorcinol bis(diphenyl phosphate)
  • BDP bisphenol A bisdiphenyl
  • a preferred organic metal phosphinate is aluminum tris(diethylphosphinate).
  • a preferred inorganic metal hypophosphite is aluminum hypophosphite.
  • flame retardants that can be used are carbon formers, particularly preferably phenol-formaldehyde resins, polycarbonates, polyimides, polysulfones, polyethersulfones or polyether ketones, as well as anti-drip agents, in particular tetrafluoroethylene polymers.
  • halogen-containing flame retardants can be used.
  • Preferred halogen-containing flame retardants are commercially available organic halogen compounds, particularly preferably ethylene-1,2-bistetrabromophthalimide, decabromodiphenylethane, tetrabromobisphenol A epoxy oligomer, tetrabromobisphenol A oligocarbonate, tetrachlorobisphenol A oligocarbonate, polypentabromobenzyl acrylate, brominated polystyrene or brominated polyphenylene ethers, which can be used alone or in combination with synergists, in particular antimony trioxide or antimony pentoxide, where Among the halogen-containing flame retardants, brominated polystyrene is particularly preferred.
  • Brominated polystyrene is preferably used in amounts in the range from 10 to 30% by weight, particularly preferably in amounts in the range from 15 to 25% by weight, in each case based on the total composition, with at least one of the other components being reduced to such an extent that the sum of all percentages by weight always amounts to 100.
  • Brominated polystyrene is commercially available in various product qualities. Examples include Firemaster® PBS64 from Lanxess, Cologne, Germany, and Saytex® HP-3010 from Albemarle, Baton Rouge, USA.
  • At least one additive is used in the polymer compositions in addition to the polyester and the colorant.
  • Additives to be used with preference are antioxidants, thermal stabilizers, UV stabilizers, gamma ray stabilizers, components for reducing water absorption or hydrolysis stabilizers, antistatic agents, emulsifiers, nucleating agents, plasticizers, processing aids, impact modifiers, lubricants and/or mold release agents, components for reducing water absorption, flow aids or elastomer modifiers, chain-extending additives, and colorants other than 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one.
  • the additives can be used alone or in a mixture or in the form of masterbatches.
  • thermal stabilizers as additives are sterically hindered phenols, in particular those containing at least one 2,6-di-tert-butylphenyl group and/or 2-tert-butyl-6-methylphenyl group, and also phosphites, hypophosphites, in particular sodium hypophosphite NaH2PO2, hydroquinones, aromatic secondary amines, substituted resorcinols, salicylates, benzotriazoles and benzophenones, 3,3'-thiodipropionic acid esters and variously substituted representatives of these groups or mixtures thereof.
  • the thermal stabilizers to be used as additives are preferably used in amounts of 0.01 to 2 parts by mass, particularly preferably 0.05 to 1 part by mass, in each case based on 100 parts by mass of polyester.
  • UV stabilizers to be used as additives are preferably substituted resorcinols, salicylates, benzotriazoles and benzophenones, HALS derivatives (“hindered amine light stabilizers”) containing at least one 2,2,6,6-tetramethyl-4-piperidyl unit or benzophenones.
  • the UV stabilizers to be used as additives are preferably in an amount of 0.01 to 2 parts by mass, particularly preferably in an amount of 0.1 to 1 part by mass, in each case based on 100 parts by mass of polyester.
  • Colorants to be used as additives and other than 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one are preferred, inorganic pigments, in particular ultramarine blue, bismuth vanadate, iron oxide, titanium dioxide, zinc sulfide, tin-titanium-zinc oxides [CAS No. 923954-49-8], furthermore organic colorants, preferably phthalocyanines, quinacridones, benzimidazoles, in particular Ni-2-hydroxy-naphthyl-benzimidazole [CAS No.
  • nucleating agents as additives are sodium or calcium phenylphosphinate, aluminum oxide or silicon dioxide and, most preferably, talc, although this list is not exhaustive.
  • Preferred plasticizers to be used as additives are dioctyl phthalate, dibenzyl phthalate, butylbenzyl phthalate, hydrocarbon oils or N-(n-butyl)benzenesulfonamide.
  • Elastomer modifiers preferably used as additives include one or more graft polymers of
  • the graft base E.2 generally has an average particle size d50 value of 0.05 to 10 pm, preferably 0.1 to 5 pm, particularly preferably 0.2 to 1 pm, determined by means of laser diffraction in accordance with ISO 13320.
  • Monomers of E.1 are preferably mixtures of
  • E.1.2 1 to 50 wt.% vinyl cyanides, in particular unsaturated nitriles such as acrylonitrile and methacrylonitrile, and/or (meth)acrylic acid (Ci-Cs)-alkyl esters, in particular
  • Preferred monomers E.1.1 are selected from at least one of the monomers styrene, a-methylstyrene and methyl methacrylate
  • preferred monomers E.1.2 are selected from at least one of the monomers acrylonitrile, maleic anhydride, glycidyl methacrylate and methyl methacrylate.
  • Particularly preferred monomers are E.1.1 styrene and E.1.2 acrylonitrile.
  • Suitable graft bases E.2 for the graft polymers used in the elastomer modifiers are diene rubbers, EPDM rubbers, i.e. those based on ethylene/propylene and optionally diene, and also acrylate, polyurethane, silicone, chloroprene and ethylene/vinyl acetate rubbers.
  • EPDM stands for ethylene-propylene-diene rubber.
  • Preferred grafting bases E.2 are diene rubbers, in particular based on butadiene, isoprene, etc. or mixtures of diene rubbers or copolymers of diene rubbers or mixtures thereof with other copolymerizable monomers, in particular according to E.1.1 and E.1.2, with the proviso that the glass transition temperature of component E.2 is ⁇ 10°C, preferably ⁇ 0°C, particularly preferably ⁇ -10°C.
  • Lubricants and/or mold release agents to be used as additives are preferably long-chain fatty acids, in particular stearic acid or behenic acid, their salts, in particular Ca or Zn stearate, and their ester derivatives, in particular those based on pentaerythritol, in particular fatty acid esters of pentaerythritol or amide derivatives, in particular ethylene-bis-stearylamide, montan waxes and low molecular weight polyethylene or polypropylene waxes.
  • Montan waxes in the sense of the present invention are mixtures of straight-chain, saturated carboxylic acids with chain lengths of 28 to 32 C atoms.
  • Glass fiber reinforced electromobility components preferably relates to electromobility components based on polymer compositions in which, in addition to the polyester and the colorant, glass fibers are used as a filler or reinforcing material, preferably cut long glass fibers with an average initial length in the range of 1 to 50 mm, to be determined by means of laser diffraction particle size analysis (laser granulometric measurement or laser diffractometry) according to ISO 13320.
  • the present invention relates to electromobility components based on polymer compositions in which, in addition to the polyester and the colorant, cut long glass fibers with an average initial length in the range of 1 to 10 mm, very particularly preferably in the range of 2 to 7 mm, to be determined by means of laser diffraction particle size analysis (laser granulometric measurement or laser diffractometry) according to ISO 13320, are used as filler or reinforcing material.
  • laser diffraction particle size analysis laser granulometric measurement or laser diffractometry
  • 1 to 150 parts by mass, preferably 5 to 80 parts by mass, particularly preferably 10 to 50 parts by mass of glass fibers are used in the polymer compositions per 100 parts by mass of polyester.
  • the glass fibers to be used as filler or reinforcing material have an average fiber diameter determined by laser diffraction according to ISO 13320 in the range from 7 to 18 pm, particularly preferably in the range from 9 to 15 pm.
  • the invention particularly preferably relates to electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number starting with "2" in the RAL color table based on polymer compositions containing at least one polyester and a colorant with an average particle size d50 in the range from 1 to 12 pm to be determined according to ISO 13320 by means of laser diffraction, containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 and glass fibers, preferably chopped long glass fibers with a particle size analysis determined by means of laser diffraction (laser granulometric measurement or laser diffractometry) according to ISO 13320 in the range from 1 to 50 mm, particularly preferably in the range from 1 to 10 mm, very particularly preferably in the range from
  • the invention also relates to a method for producing electromobility components with a color difference AE ⁇ 20 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2”, by mixing at least one polyester and one colorant to form polymer compositions, extruding them into strands, cooling them until they can be granulated, drying them and granulating them, and then further processing the polymer compositions by injection molding, including the special processes gas injection technology (GIT), water injection technology (WIT) or projectile injection technology (PIT), in extrusion processes, including profile extrusion, or by blow molding, wherein
  • GIT gas injection technology
  • WIT water injection technology
  • PIT projectile injection technology
  • the electromobility components also have a color distance AE ⁇ 10 from the L*a*b* coordinates to a color number of the RAL color table beginning with "2", particularly preferably AE ⁇ 5.
  • the invention most preferably relates to a process in which, in addition to components A) and B), C) glass fibers with an average initial length in the range from 1 to 50 mm, particularly preferably in the range from 1 to 10 mm, very particularly preferably in the range from 2 to 7 mm, to be determined by means of laser diffraction particle size analysis (laser granulometric measurement or laser diffractometry) according to ISO 13320 are used.
  • laser diffraction particle size analysis laser granulometric measurement or laser diffractometry
  • laser diffraction particle size analysis laser granulometric measurement or laser diffractometry
  • the glass fibers also have an average fiber diameter, determined by means of laser diffraction according to ISO 13320, in the range from 7 to 18 pm, particularly preferably in the range from 9 to 15 pm.
  • the isomer mixture to be used as a colorant is preferably used in combination with glass fibers.
  • the invention relates to the use of a colorant in polymer compositions containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range of 1 to 12 pm to be determined by means of laser diffractometry according to ISO 13320 as a colorant for obtaining color streak-reduced polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number beginning with "2" of the RAL color table, wherein for 100 parts by mass of at least one polyester, preferably polybutylene terephthalate, 0.01 to 5 parts by mass of the isomer mixture and 1 to 150 parts by mass, preferably 5 to 80 parts by
  • the invention preferably relates to the use of a colorant in polymer compositions containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined by means of laser diffractometry according to ISO 13320 to obtain color streak-reduced polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number starting with "2" in the RAL color table and a color number according to DIN EN ISO 11664-4 to be determined AC* > 1 to a corresponding comparison sample whose isomer ratio is not in the range of 1 : 1 : 0.8 - 1 .5 to 1 : 1 .
  • the invention particularly preferably relates to the use of a colorant in polymer compositions containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined by laser diffractometry according to ISO 13320 to obtain color-streak-free polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number of the RAL color table beginning with "2" and an AC* > 1 to be determined according to DIN EN ISO 11664-4 to a corresponding comparison sample outside the above isomer ratio, wherein for 100 parts by mass of at least one polyester, preferably at least polybutylene terephthalate, 0.
  • the invention particularly preferably relates to the use of a colorant in polymer compositions containing the isomer mixture of 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:1:0.8-1.5 to 1:1.5:0.8-1.5 with an average particle size d50 in the range from 1 to 12 pm to be determined by means of laser diffractometry according to ISO 13320 to obtain color-streak-free polyester-based electromobility components with a color difference AE ⁇ 20, preferably AE ⁇ 10, in particular AE ⁇ 5, from the L*a*b* coordinates to a color number beginning with "2" of the RAL colour table and a (colour) brilliance to be determined according to DIN EN ISO 11664-4 with an AC* > 1 to a corresponding comparison sample whose isomer ratio is not in the range of 1 : 1 : 0.8 - 1 .
  • the C* value according to DIN EN ISO 11664-4 was to be determined using a d/8° spectrophotometer in a coloristic measurement ( D65 standard light, CIE 1976 L*a*b* Color Space) for the different isomer distributions, determined via HPLC (high pressure liquid chromatography), as a measure of the color brilliance of the molding compounds described in Table I in the form of 60*40*2 mm 3 plates.
  • HPLC high pressure liquid chromatography
  • the average particle size d50 according to IS0 13320 was to be determined as a measure of the reduction of color streaks.
  • HPLC is a liquid chromatography method with which one can not only separate substances, but also identify and quantify them using standards (determine the exact concentration), see: https://de.wikipedia.org/wiki/Hoch tedioussfl%C3%BCsstechnikschromatographie
  • Polyester Polybutylene terephthalate Pocan® B1505, Lanxess
  • Component B' Colorant with an average particle size d50 in the range of 18.7 pm, determined by laser diffractometry according to ISO 13320, containing the isomers 9,9'-oxybis-12H-phthaloperin-12-one, 9,10-oxybis-12H-phthaloperin-12-one and 10,10'-oxybis-12H-phthaloperin-12-one in a ratio of 1:2:1, prepared according to synthesis procedure 1
  • Example 1 The results in Table I show an improvement in color brilliance and a reduction in the average particle size d50 in Example 1 according to the invention compared to non-inventive comparison 1.
  • the plastic sheets examined in Example 1 according to the invention had a RAL color value of 2001 with an AE of ⁇ 10.
  • using a colorant with an inventive isomer ratio in the form of component B Example 1 showed a clear reduction (-) in streaking that was visible to the naked eye compared to using component B' as a colorant (comparison 1) with clear streaking that was visible to the naked eye (+).
  • the reaction product was isolated on a suction filter and then stirred in 300 g of phenol at 175°C for 45 minutes. Then, at a temperature of 175°C, 295 g of methanol were added and the temperature of the reaction mixture was cooled to 30°C over the course of three hours.
  • the reaction product was isolated on a suction filter and washed first with 440 g of methanol and then with 800 g of water and dried in a vacuum drying cabinet at 80°C and 150 mbar.
  • the isomer distribution of the dye was determined to be 1:1, 2:1 and the average particle size d50 was determined to be 5 pm.
  • the respective coloured granulate was dried at 120°C for 4 hours and from the respective dried, coloured granulate, sample plates measuring 4cm x 6cm x 0.2cm were produced on an injection moulding machine at 230 to 270°C melt temperature, 10 bar dynamic pressure and 80°C mould temperature. After at least ten injection cycles, sample plates were produced for The color measurement was taken and left to rest at room temperature for at least 1 hour. The reflectance measurements were then carried out on the sample plates using a d/8° spectrophotometer. An improvement in (color) brilliance within the meaning of the present invention was present if the AC* compared to a comparison measurement based on a preparation outside the claimed isomer ratio was > 1, because an AC* of 1 is already visible to the naked eye.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne des composants pour l'électromobilité ayant une différence de couleur ΔE < 20 entre les coordonnées L *a*b et un nombre de couleurs débutant à "2" du nuancier RAL,contenant des compositions polymères sur la base d'au moins un polyester et un pigment présentant une grosseur de particules moyenne d50, déterminée selon ISO 13320 au moyen d'une diffractométrie laser, dans la plage de 1 à 12 μm, contenant 9,9'-oxybis-12H-phtalopérin-12-one, 9,10-oxybis-12H-phtalopérin-12-one et 10,10'-oxybis-12H-phtalopérin-12-one dans un ratio de 1:1:0.8-1.5 à 1:1.5:0.8-1.5. L'invention concerne également l'utilisation d'un pigment présentant une taille de particules moyenne d50, déterminée selon ISO 13320, dans la plage de 1 à 12 μm, contenant 9,9'-oxybis-12H-phtalopérin-12-one, 9,10-oxybis-12H-phtalopérin-12-one et 10,10'-oxybis-12H-phtalopérin-12-one dans un ratio de 1:1:0.8-1.5 à 1:1.5:0.8-1.5, dans des compositions polymères pour la production de composants pour l'électromobilité à base de polyester ayant une différence de couleur ΔE < 20 entre les coordonnées L *a*b et un nombre de couleurs débutant à "2" du nuancier RAL, en particulier afin de réduire l'effet de couleurs croisées dans la production de composants pour l'électromobilité à base de polyester.
PCT/EP2024/074456 2023-10-25 2024-09-02 Composants pour l'électromobilité Pending WO2025003531A1 (fr)

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