WO2008037444A1 - Mélanges maîtres anticondensation hautement chargés produits à partir de cires à base de métallocène - Google Patents

Mélanges maîtres anticondensation hautement chargés produits à partir de cires à base de métallocène Download PDF

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Publication number
WO2008037444A1
WO2008037444A1 PCT/EP2007/008365 EP2007008365W WO2008037444A1 WO 2008037444 A1 WO2008037444 A1 WO 2008037444A1 EP 2007008365 W EP2007008365 W EP 2007008365W WO 2008037444 A1 WO2008037444 A1 WO 2008037444A1
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Prior art keywords
metallocene
waxes
wax
masterbatch according
masterbatch
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PCT/EP2007/008365
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German (de)
English (en)
Inventor
Reinhold Kling
Pirko Kolditz
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Clariant Finance (Bvi) Limited
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Publication of WO2008037444A1 publication Critical patent/WO2008037444A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06—Waxes
    • 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
    • C08J2491/00—Characterised by the use of oils, fats or waxes; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2314/00—Polymer mixtures characterised by way of preparation
    • C08L2314/06—Metallocene or single site catalysts

Definitions

  • the present invention relates to the preparation of highly charged anti-condensation masterbatches, which may be low-melting or liquid anti-condensation agents. With these substances, the quality of the plastics is significantly influenced, it can the end products increased transparency - the water pearls better off - to be given a better sliding behavior and greater flexibility.
  • the invention relates to the use of copolymeric low molecular weight waxes for the preparation of such masterbatches, in which the waxes are prepared by means of metallocene catalysts having a low dropping point, high transparency and low viscosity.
  • the incorporation of the anti-condensation agent is much easier, the process temperatures can be kept significantly lower, so that a much higher loading than previously possible and can be dispensed with a polymeric carrier.
  • strand granulation which is common for many masterbatch producers, can be used for these highly charged anti-condensation masterbatches.
  • glycerol or sorbitan esters or blends are often used. It is triggered by a targeted water film on the film, the known negative effect of water pearls disappears, the film has a higher clarity.
  • the incorporated products should be optimally distributed, the carrier should be optimally compatible with the polymer, the active substance should only be present on the surface to a limited extent, so that there is little clumping / fouling tendency, with as high a dosage as possible in order to keep the raw material costs as low as possible.
  • melt mixture can be carried out in a suitable extruder or in kneaders. This is followed by granulation, grinding or spraying.
  • a cold mixture consists of suitable polymer supports, such as polyethylene, polypropylene or ethylene-vinyl acetate copolymer and the like, and may additionally contain waxes, fatty acid derivatives, stearates, etc.
  • suitable polymer supports such as polyethylene, polypropylene or ethylene-vinyl acetate copolymer and the like, and may additionally contain waxes, fatty acid derivatives, stearates, etc.
  • the disadvantage of these polymer blends is that the proportion of polymer allows a higher addition short-chain components only limited, the saturation range is exceeded, and this can often already be above 15%, there is a separation of polymer and the Konkondensationszutschstoffes, the viscosity differences are too large. The incorporation is no longer uniform, the strand strength of the masterbatches produced is lower.
  • JP 08053549 describes that in a polyolefin up to 200 parts of a liquid modifier and up to 20 wt .-% of an organic gelling agent is introduced. The masterbatch is made under heat and kneading of the aggregates and the polymer is added in small doses.
  • JP 05271427 describes that the thermoplastic and the migrating additive are dissolved in a solution. The mixture is then cooled, the gel is pulverized and the solvent is removed. This is followed by a heat treatment and drying under vacuum to finally have a masterbatch with a charge of 50 wt .-% active substance.
  • the object of the present invention was to load masterbatches with the highest possible proportion of liquid, low-melting or low-viscosity anti-condensation agents in order to bring about the production of plastic components with a high antifogging effect, good release effect and good sliding properties, economically and ecologically advantageously, and thus products to deliver high quality.
  • the masterbatches produced in much more different polymers, different chemical composition than before, can be used because less Compatibility problems due to the high loading are present.
  • the wax carrier should also allow easier incorporation and dispersion into the polymers, resulting in a more even distribution at the product surface.
  • This object is achieved in accordance with the invention by incorporating the anticondensation component into a metallocene wax, a mixture of metallocene waxes, a mixture of metallocene wax with Ziegler wax or a wax polymer blend.
  • the main constituent of the wax carrier is a metallocene wax.
  • Metallocene waxes or metallocene polyolefin waxes are by definition waxes prepared in the presence of metallocenes as a catalyst. The composition so prepared is compounded by extrusion into an anti-condensation masterbatch.
  • the present invention is an Anitikondensationsmasterbatch, of the type mentioned, comprising i) one or more anti-condensation agents ii) one or more metallocene Polyolefinwachse iii) one or more waxes selected from polar and non-polar non-metallocene polyolefin waxes and
  • the masterbatch according to the invention may, if required, also contain quantities of fillers, such as silica, talc or additives, such as HALS and UV absorbers, of from 0 to 30% by weight, based on the total weight of the masterbatch.
  • fillers such as silica, talc or additives, such as HALS and UV absorbers
  • the masterbatch according to the invention thus has a particularly high anti-condensation agent and filler content, it has a very good compatibility with the starting polymers and largely excludes negative effects on the mechanical properties.
  • the metallocene waxes have a melt viscosity, measured at a temperature of 170 ° C., in the range from 40 to 80,000 mPas, preferably from 45 to 35,000 mPas, particularly preferably from 50 to 10,000 mPas.
  • All the waxy components of the masterbatch are melt 80-170 0 C.
  • Anti-condensation compositions preferred according to the invention contain from 20 to 75% by weight, preferably from 25 to 70% by weight of a polyglycerol or another anticondensating agent, and from 25 to 80% by weight, preferably from 30 to 75% by weight, of the metallocene polyolefin wax, 0.1 to 30 wt .-%, preferably 0.5 to 25 wt .-% of one or more non-metallocene waxes.
  • the erfmdungswashe masterbatch may contain certain amounts of fillers, such as silica, talc or additives such as HALS and UV absorbers or organic, inorganic dyes or pigments, between 0 to 30 wt .-%, based on the total weight of the masterbatch.
  • fillers such as silica, talc or additives such as HALS and UV absorbers or organic, inorganic dyes or pigments, between 0 to 30 wt .-%, based on the total weight of the masterbatch.
  • the waxes prepared as catalyst in the presence of metallocene are copolymer waxes of propylene and 0.1 to 50% of ethylene and / or 0.1 to 50% of at least one branched or unbranched 1-alkene with 4 to
  • the metallocene waxes prepared in the presence of metallocene as a catalyst are largely or completely amorphous and can additionally be polar modified if necessary.
  • non-metallocene polyolefin waxes on the one hand, ethylene vinyl acetate in particular waxes with a dropping point between 90 and 120 0 C, a vinyl acetate content of 1 to 30% and a viscosity of 50 to 3,000 mPa-s, preferably from 50 to 1 500 mPa-s, at a temperature of 140 0 C, on the other hand also non-polar, but also polar non-metallocene waxes having a dropping point in the range of 90 to 120 0 C and a viscosity of less than 30,000 mPa-s, preferably less than 15,000 mPa-s, at a temperature of 140 0 C, suitable.
  • Suitable non-metallocene polyolefin waxes are homopolymers of ethylene or higher 1-olefins having 3 to 10 carbon atoms or copolymers thereof with one another.
  • the polyolefin waxes preferably have a weight-average molar mass M w of between 1,000 and 20,000 g / mol and a number-average molar mass M n of between 500 and 15,000 g / mol.
  • Metallocene compounds of the formula I are used for the preparation of the metallocene polyolefin waxes used according to the invention.
  • This formula also includes compounds of the formula Ia,
  • M 1 is a Group IVb, Vb or VIb metal of the Periodic Table, for example, titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum, tungsten, preferably titanium, zirconium, hafnium.
  • R 1 and R 2 are identical or different and denote a hydrogen atom, a C 1 -C 10 , preferably C 1 -C 3 -alkyl group, in particular methyl, a Ci-Ci 0 -, preferably Ci-C3-Alkoxygmppe, a C 6 -Ci O , preferably C ⁇ -CB-aryl group, a C-6-C- ⁇ o-, preferably C 6 -C 8 -aryloxy, a C 2 -C 0 , preferably C 2 -C 4 -alkenyl, a C 7 -C 40 -, preferably C 7 -C 0 arylalkyl group, a C 7 -C 40 -, preferably C 7 -C 2 alkylaryl group, a Cs-C 40 -, preferably C 8 -C 2 -arylalkenyl group or a halogen, preferably a chlorine atom ,
  • R 3 and R 4 are identical or different and denote a mononuclear or polynuclear hydrocarbon radical which can form a sandwich structure with the central atom M 1 .
  • R 3 and R 4 are preferably cyclopentadienyl, indenyl, tetrahydroindenyl, benzoindenyl or fluorenyl, it being possible for the basic units to carry additional substituents or to bridge them with one another.
  • one of the radicals R 3 and R 4 may be a substituted nitrogen atom, wherein R 24 has the meaning of R 17 and is preferably methyl, tert-butyl or cyclohexyl.
  • R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are identical or different and denote a hydrogen atom, a halogen atom, preferably a fluorine, chlorine or bromine atom, a Ci-Ci 0 -, preferably C ⁇ -C 4 alkyl group, a C 6 -C 0 -, preferably C 6 -C 8 aryl group, a Ci-Ci 0 -, preferably Ci-C 3 alkoxy group, a -NR 16 2 -, -SR 16 - , -OSiR 1 V, -SiR 1 V or -PR 16 2 radical, wherein R 16 is a Ci-Ci 0 -, preferably Ci-C 3 alkyl group or C- 6 -C 10 -, preferably C 6 -C 8 -Aryl group or in the case of Si or P-containing radicals is also a halogen atom, preferably chlorine atom or two adjacent radicals R 5
  • R 17 , R 18 and R 19 are identical or different and a hydrogen atom, a halogen atom, preferably a fluorine, chlorine or bromine atom, a C 1 -C 30 , preferably C 1 -C 4 -alkyl, in particular methyl, a Cio-fluoroalkyl, preferably CF 3 group, a C 6 -Cio-fluoroaryl, preferably pentafluorophenyl, a C 6 -C 0, preferably C 6 -C 8 -aryl, a C 1 -Ci 0 -, preferably Ci C 4 alkoxy, in particular methoxy, a C 2 -C 10 , preferably C 2 -C 4 alkenyl,
  • M 2 is silicon, germanium or tin, preferably silicon and germanium.
  • R 11 and R 12 are the same or different and have the meaning given for R 17 , m and n are the same or different and are zero, 1 or 2, preferably zero or 1, where m plus n is zero, 1 or 2, preferably zero or 1.
  • R 14 and R 15 have the meaning of R 17 and R 18 .
  • suitable metallocenes are:
  • Dimethylsilyl-bis-1- zirconium dichloride (2-methyl-4,5-benzoindenyl) Dimethylsilyl-bis-1- (2-methyl-4-ethylindenyl) zirconium dichloride, dimethylsilyl-bis-1- (2-methyl-4-i-propylindenyl) zirconium dichloride, dimethylsilyl-bis-1- (2-methyl-4-phenylindenyl ) zirconium dichloride, dimethylsilyl-bis-1- (2-methyl-indenyl) zirconium dichloride, dimethylsilyl-bis-1- (2-methyltetrahydroindenyl) zirconium dichloride, dimethylsityl-bis-1-indenylzirconium dichloride, dimethylsilyl-bis-1-indenylzirconium dimethyl, dimethylsilyl-bis 1-tetrahydroindenylzirconium dichloride, diphenylmethylene---fluorenyl
  • Suitable cocatalysts for metallocenes of the formula I are organoaluminum compounds, in particular aluminoxanes or else aluminum-free systems such as R 2O ⁇ NH 4- ⁇ BR 21 4, R 2O ⁇ PH 4- ⁇ BR 21 4, R 20 3 CBR 21 4 or BR 21.
  • x is a number from 1 to 4
  • the radicals R 20 are identical or different, preferably identical, and are C 1 -C 10 -alkyl or C 6 -C 8 -aryl or two radicals R 20 together with the atom connecting them Ring
  • the radicals R 21 are the same or different, preferably the same, and are C ⁇ -Ci ⁇ -aryl, which may be substituted by alkyl, haloalkyl or fluorine.
  • R 20 is ethyl, propyl, butyl or phenyl and R 21 is phenyl, pentafluorophenyl, 3,5-bis-trifluoromethylphenyl, mesityl, xylyl or ToIyI.
  • organoaluminum compound such as triethylaluminum, tributylaluminum and others and mixtures are suitable.
  • supported single-center catalysts can also be used. Preference is given to catalyst systems in which the residual contents of support material and cocatalyst do not exceed a concentration of 100 ppm in the product.
  • melt viscosities were determined according to DIN 53019 with a rotary viscometer, the dropping points according to DIN 51801/2, the softening points ring / ball according to DIN EN 1427.
  • the drop point determination is carried out with a drop point device according to Ubbelohde according to DIN 51801/2, the softening point ring / ball according to DIN EN 1427.
  • the anticondensation masterbatches according to the invention may, as already mentioned above, additionally be used fillers such as zeolites, silicic acid, montmorillonites, bentonites, silicates such as aluminum silicates, sodium silicate, calcium silicates, nanoclay, talc, CaCO 3. Likewise, further adjuvants such as stearates, antioxidants, antistatic agents, oleic acid amide, glycerol fatty acid partial esters, stearates, slip agents may be present in small amounts.
  • the anti-condensation masterbatches according to the invention may additionally contain auxiliaries such as UV absorbers, nickel stabilizers, sterically hindered amines (HALS products) and combinations thereof. This applies to all products listed in Additive Handbook Edition No. 5 (Edition 2000).
  • Suitable colorants are organic and inorganic dyes and pigments.
  • organic dyes and pigments preference is given to using azo or disazo pigments, laked azo or disazo pigments or polycyclic pigments, preferably phthalocyanine, quinacridone, perylene, dioxazine, anthraquinone, thioindigo, diaryl or quinophthalone pigments.
  • Suitable inorganic dyes and pigments are metal oxides suitable for pigmentation, mixed oxides, aluminum sulfates, chromates, metal powders, pearlescent pigments (mica), luminous colors, titanium oxides, cadmium-lead pigments, preferably iron oxides, carbon black, silicates, nickel titanates, cobalt pigments or chromium oxides.
  • Nonionic surfactants such as glycerol, polyglycerol sorbitan esters, ethoxylated sorbitan esters or mixtures thereof and combinations with distilled monoglyceride are used as anti-condensation agents.
  • the required proportion of metallocene waxes depends on the additive-matrix exchange reaction, on the surface structure of the anti-condensation agent, on the end-part properties, on the surface structure of the finished article, in particular on the optical properties, as well as on the processing properties.
  • the present invention also relates to a process for producing the masterbatch according to the invention by combining the constituents and subsequent homogenization in an extruder. Pre-mixing of the individual components is an important prerequisite for product production and can be carried out at room temperature in a suitable mixing apparatus. This phase lasts about 3 to 10 minutes, preferably 5 to 7 minutes.
  • the anti-condensation masterbatch preparation it is also expedient to work with an initial mixing process.
  • a mixture of the active ingredient composition according to the invention produced.
  • the mixture is done with appropriate mixing technique.
  • the preparation of mixtures can be omitted, however, by feeding the individual components of a recipe directly to the extrusion plant.
  • the said mixture is then fed by means of a suitable metering device to an extrusion plant.
  • these are single or twin-screw extruders, but it is also possible to use continuous and discontinuous kneaders or compactors.
  • the subsequent granulation takes place via strand and Kopfgranulmaschine, but also spraying is possible.
  • preparations can also be blended with each other or with plastic in a second extrusion pass.
  • polyolefins for example, polyolefins, ethylene-vinyl acetate copolymers (EVA), polyolefin blends, polyvinyl chloride (PVC), polyethylene terephthalate (PET), polybutylene glycol terephthalate (PBT) and their copolyesters, and special polymers.
  • EVA ethylene-vinyl acetate copolymers
  • PVC polyvinyl chloride
  • PET polyethylene terephthalate
  • PBT polybutylene glycol terephthalate
  • a metallocene wax prepared from the waxes metallocene-PP wax was used.
  • the products are used in fine-grained state or in granular form.
  • polyolefins a) -c) used according to the invention and listed in Table 1 were obtained by copolymerization of propylene with ethylene with the
  • Metallocene catalyst Dimethylsilylbisindenylzirconium dichloride after the in EP-AO 384 264 (general rule Examples 1 to 16). The different softening points and viscosities were adjusted by varying the ethylene input and the polymerization temperature.
  • blowing agent composition according to the invention was prepared as described below:
  • the filler was mixed with the wax.
  • Metallocene wax was in each case the above described wax used, the addition of the anti-condensation agent was carried out via a sidefeeder:
  • the anti-condensation masterbatches according to Preparation Examples 1 to 3 were adjusted and prepared in a co-rotating twin screw with a special screw design and with a low temperature image to form masterbatches, which lead to a quality improvement in different polymers. This is mainly a reduced droplet formation on the film surface, increased transparency, and a better sliding behavior, and a higher flexibility of the plastics.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Combustion & Propulsion (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention concerne une composition de substances actives présentant une teneur élevée en agents anticondensation liquides ou s'écoulant facilement et une ou plusieurs cires de polyoléfine, la proportion quantitativement plus élevée étant représentée par une cire à base de métallocène et les autres cires étant des cires de polyoléfine polaires ou non polaires non à base de métallocène. L'ensemble des cires de polyoléfine représente au moins 10 % en poids de la formulation et leur point de fusion se situe entre 80 et 170 °C. La composition de substances actives selon l'invention présente une teneur réduite en poussières et est utilisée pour la production de mélanges maîtres.
PCT/EP2007/008365 2006-09-30 2007-09-26 Mélanges maîtres anticondensation hautement chargés produits à partir de cires à base de métallocène WO2008037444A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006046564A DE102006046564A1 (de) 2006-09-30 2006-09-30 Hochgeladene Antikondensationsmasterbatche durch den Einsatz von Metallocen-Wachsen
DE102006046564.4 2006-09-30

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853549A (ja) * 1994-08-11 1996-02-27 Tokyo Ink Kk 液状改質剤含有マスターバッチ及びその製法
DE10063423A1 (de) * 2000-12-20 2001-07-12 Clariant Gmbh Dispergierung von Pigmenten in Polyolefinen
US20030127625A1 (en) * 2001-03-01 2003-07-10 Hiroshi Nagasawa Antifogging agent composition
EP1619010A1 (fr) * 2004-07-23 2006-01-25 Clariant GmbH Utilisation de cires de polyoléfine dans des polycondensats

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0853549A (ja) * 1994-08-11 1996-02-27 Tokyo Ink Kk 液状改質剤含有マスターバッチ及びその製法
DE10063423A1 (de) * 2000-12-20 2001-07-12 Clariant Gmbh Dispergierung von Pigmenten in Polyolefinen
US20030127625A1 (en) * 2001-03-01 2003-07-10 Hiroshi Nagasawa Antifogging agent composition
EP1619010A1 (fr) * 2004-07-23 2006-01-25 Clariant GmbH Utilisation de cires de polyoléfine dans des polycondensats

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