DE10009754A1 - Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion - Google Patents

Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion

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Publication number
DE10009754A1
DE10009754A1 DE10009754A DE10009754A DE10009754A1 DE 10009754 A1 DE10009754 A1 DE 10009754A1 DE 10009754 A DE10009754 A DE 10009754A DE 10009754 A DE10009754 A DE 10009754A DE 10009754 A1 DE10009754 A1 DE 10009754A1
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DE
Germany
Prior art keywords
waxes
dollar
use according
polyolefin
sorbitol
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.)
Withdrawn
Application number
DE10009754A
Other languages
German (de)
Inventor
Manfred Schmalzl
Gabriele Sluiter
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant 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
Application filed by Clariant GmbH filed Critical Clariant GmbH
Priority to DE10009754A priority Critical patent/DE10009754A1/en
Priority claimed from DE2001508749 external-priority patent/DE50108749D1/en
Publication of DE10009754A1 publication Critical patent/DE10009754A1/en
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C09D191/06Waxes
    • C09D191/08Mineral waxes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/03Printing inks characterised by features other than the chemical nature of the binder
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/02Printing inks
    • C09D11/12Printing inks based on waxes or bitumen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/04Homopolymers or copolymers of ethene
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/10Homopolymers or copolymers of propene
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C09D191/06Waxes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00Compositions 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 a halogen; Compositions of derivatives of such polymers
    • C08L27/02Compositions 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12Compositions 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/18Homopolymers or copolymers or tetrafluoroethene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06Waxes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06Waxes
    • C08L91/08Mineral waxes

Abstract

The present invention relates to the use of mixtures of DOLLAR A a) polyolefin waxes from C¶2¶-C¶18¶-alpha-olefins, produced using metallocene catalysts, with one or more further additives selected from the group consisting of DOLLAR A b) polytetrafluoroethylene, DOLLAR A c) amide waxes, made from the reaction of diethylenamine with saturated and unsaturated fatty acids, DOLLAR A d) montan waxes including acid and ester waxes with a carbon chain length of the carboxylic acid from C¶24¶ to C¶34¶, DOLLAR A e) natural plant waxes, DOLLAR A f) reaction products of sorbitol (sorbitol) with saturated and / or unsaturated fatty acids and / or montanic acids, DOLLAR A g) synthetic hydrocarbons, DOLLAR A h) paraffins and microcrystalline waxes, which are obtained from petroleum refining and DOLLAR A i) polar polyolefin waxes, produced by oxidation or grafting of ethylene or DOLLAR A propylene homopolymer and copolymer waxes for the production of printing inks.

Description

The present invention relates to the use of means Metallocene catalysts produced polyolefin waxes in combination with PTFE, Amide waxes, montan waxes, natural plant waxes, sorbitol esters, synthetic hydrocarbon waxes, micro and macro crystalline paraffins, polar polyolefin waxes as an additive component in printing inks.

In printing inks, waxes have the task of abrasion, scouring and Increase scratch resistance of printed matter. The waxes are usually in the form of solvent dispersions or pastes or in solid form micronized form used. Micronization occurs either through Grinding on suitable mills or spraying from the melt, in each case if necessary with subsequent classification. The necessary average particle sizes are usually below 10 µm.

To date, waxes of various types have been found for this application Manufacturing process use. It is common - in addition to the thermal degradation of high molecular weight polyolefins or radical ethylene polymerization high pressures and temperatures - the production of waxes by ethylene or propylene homo- or copolymerization with Ziegler-Natta catalysts a titanium compound as a catalytically active species, such as in DE-A-15 20 914 discloses.

EP-A-0 890 619 discloses that in particular the use of Metallocene catalyst systems in the manufacture of polyolefin waxes Materials leads to improved abrasion protection effects when used in printing inks cause.  

The use of pure using metallocene catalysis Polyolefin waxes in printing inks cover the basic requirements for one improved abrasion protection compared to the original printing ink. In addition, there are applications that look for specially improved Abrasion protection or high surface gliding effect or good overprintability request e.g. B. when printing abrasive, matt-coated papers or in Packaging printing area.

Surprisingly, it has now been found that polyolefin waxes are produced using of metallocene catalysts, in combination with additives this increased Meet the requirements profile in a special way.

The present invention relates to the use of mixtures of

  • a) polyolefin waxes from C 2 -C 18 -α-olefins, produced using metallocene catalysts, with one or more further additives, selected from the group consisting of
  • b) polytetrafluoroethylene,
  • c) amide waxes,
  • d) Montan waxes including acid and ester waxes with a carbon chain length of the carboxylic acid from C 22 to C 36
  • e) natural plant waxes,
  • f) reaction products of sorbitol (sorbitol) with saturated and / or unsaturated fatty acids and / or montanic acids
  • g) synthetic hydrocarbons,
  • h) paraffins and microcrystalline waxes, which are used in petroleum refining attack,
  • i) polar polyolefin waxes, producible by oxidation of ethylene or Propylene homopolymer and copolymer waxes or their grafting with Maleic anhydride

for the production of printing inks.  

Polyolefin waxes a) are homopolymers of ethylene, propylene, Copolymers of ethylene and propylene, or copolymers of ethylene or Propylene with one or more 1-olefins in question. As 1-olefins linear or branched olefins with 4-18 C-atoms, preferably 4-6 C-atoms, used. The 1-olefins can also carry an aromatic substitution. Examples of suitable 1-olefins in addition to ethylene and propylene are 1-butene, 1-hexene, 1-octene or 1-octadecene, also styrene. Are particularly preferred Homopolymers of ethylene or propylene or copolymers of ethylene with Propylene or 1-butene. If they are copolymers, they exist preferably 70-99.9, in particular 80-99% by weight of ethylene.

Such polyolefin waxes with a dropping point between 70 and 165 ° C., in particular between 100 and 160 ° C., a melt viscosity at 140 ° C. (polyethylene waxes) or at 170 ° C. (polypropylene waxes) between 10 and 10,000 mPas, in particular between 50, are particularly preferred and 5000 mPas, and a density at 20 ° C between 0.85 and 0.96 g / cm 3 . Preferred polyolefin waxes have a molecular weight distribution M w / M n <5.

In preferred embodiments, additive b) is Polytetrafluoroethylene with a molecular weight between 30,000 and 2,000,000 g / mol, in particular between 100,000 and 1,000,000 g / mol.

In preferred embodiments, additive c) is Amide waxes, producible by reacting ammonia or ethylenediamine with saturated and / or unsaturated fatty acids. The fatty acids are for example, stearic acid, tallow fatty acid, palmitic acid or erucic acid.

Additive d) is montan waxes including acid and ester waxes with a carbon chain length of the carboxylic acid from C 22 to C 36 . The ester waxes are preferably reaction products of montanic acids with mono- or polyhydric alcohols having 2 to 6 carbon atoms, such as, for example, ethanediol, butane-1,3-diol or propane-1,2,3-triol.

In a preferred embodiment, additive e) is Carnauba wax.

In preferred embodiments, additive f) is Reaction products of sorbitol (sorbitol) with saturated and / or unsaturated Fatty acids and / or montanic acids. The fatty acids are Examples include stearic acid, tallow fatty acid, palmitic acid or erucic acid.

In preferred embodiments, additive g) is fishing Tropsch waxes.

Additive h) is paraffins and microcrystalline waxes, which incurred in oil refining. The dropping points of such paraffins are located preferably between 48 and 65 ° C, that of such microcrystalline waxes preferably between 75 and 95 ° C.

In preferred embodiments, additive i) is polar polyolefin waxes, which can be prepared by oxidation of ethylene or propylene homopolymer and copolymer waxes or their grafting with maleic anhydride. Polyolefin waxes with a dropping point between 90 and 165 ° C., in particular between 100 and 160 ° C., a melt viscosity at 140 ° C. (polyethylene waxes) or at 170 ° C. (polypropylene waxes) between 10 and 10,000 mPas, in particular between, are particularly preferred for this purpose 50 and 5000 mPas and a density at 20 ° C between 0.85 and 0.96 g / cm 3 .

The mixing ratio of component a) to components b) to i) can in Range can be varied from 1 to 99 wt .-% a) to 1 to 99 wt .-% b) to i). Becomes If a mixture of several of the components b) to i) is used, the Quantity specification for the sum of the quantities of these components.

In a preferred embodiment, the waxes are in micronized form used for the purpose of the invention.  

The metallocene catalysts for the preparation of the polyolefin waxes are chiral or nonchiral transition metal compounds of the formula M 1 L x . The transition metal compound M 1 L x contains at least one metal central atom M 1 to which at least one π ligand, e.g. B. a cyclopentadienyl ligand is bound. In addition, substituents such. B. halogen, alkyl, alkoxy or aryl groups to the metal central atom M 1 . M 1 is preferably an element of III., IV., V. or VI. Main group of the periodic table of the elements, such as Ti, Zr or Hf. Cyclopentadienyl ligand is understood to mean unsubstituted cyclopentadienyl radicals and substituted cyclopentadienyl radicals such as methylcyclopentadienyl, indenyl, 2-methylindenyl, 2-methyl-4-phenylindenyl, tetrahydroindenyl or octa-tetra-hydrofluoryl or octa-tetra-hydrofluoryl or octa. The it ligands can be bridged or unbridged, whereby single and multiple bridging - also via ring systems - are possible. The term metallocene also includes compounds with more than one metallocene fragment, so-called multinuclear metallocenes. These can have any substitution pattern and bridging variant. The individual metallocene fragments of such multinuclear metallocenes can be of the same type or different from one another. Examples of such multinuclear metallocenes are e.g. B. described in EP-A-0 632 063.

Examples of general structural formulas of metallocenes, as well as for their Activation with a cocatalyst are u. a. in EP-A-0 571 882.

The polyolefin waxes from metallocene catalysis are as follows Component 1 called, the additives b) to i) are component 2. The proportion of Component 2 in the mixture with component 1 can be between 1 to 99% amount, preferably between 5 to 50%. Mixtures can be made by grinding the two components together or by previous Mixing the components in the molten phase and subsequent Spraying or grinding.  

Examples

Table 1

Physical properties of the tested polyolefin waxes

On the basis of wax 1 and 2 and comparative wax 1, the following were: Mixtures made:

Table 2

Mixtures of polyolefin waxes with additives

The powdery starting materials were used to prepare the mixtures first premixed and then on a fluid bed counter jet mill Hosokawa Alpine AG to an average particle size below 10 microns crushed. The particle size is measured with the Laser diffraction method in a Malvern device. You can use the waxes the printing ink as a dry powder or preferably as a dispersion in Add binder solution or solvent.

Examples of ink production 1) Offset color

The mixtures M1, M2, M3, M4, M9 and M10 were incorporated in an offset ink (Novaboard® Cyan 4 C 86, BASF Drucksyseme GmbH) at 1.5% by weight with intensive stirring with a dissolver and subsequent homogenization on a three-roller . A test print (Prüfbau multi-purpose test printing machine System Dr. Dürner) was made on Phoenomatt® 115 g / m 2 paper (Scheufelen GmbH + Co KG) and the abrasion behavior was examined on a scrubber tester (scrubbing tester Prüfbau Quartant) with a scouring load of 48 g / cm 2 , scrubbing speed 15 cm / sec. The intensity of the color transferred to the test sheet after 50, 100 or 200 abrasion cycles (stroke) (color difference according to DIN 6174, measurement with Hunterlab D 25-2, Hunter) and the damage to the printed image were assessed.

Table 3

Result of the test in an offset color when incorporated as micropowder

The waxes according to the invention bring about a smaller color difference and thus improved abrasion resistance.

2) gravure ink

The mixtures M3, M4, M5, M6, M7 and M5 were incorporated at 1% by weight with intensive stirring with a dissolver into an illustration gravure ink (type RR Grav rot, Siegwerk Farbenfabrik). A test print (gravure test printer LTG 20, Einlehner testing machine construction) was made on Allgäu 60 g / m 2 paper (G. Haindl'sche Papierfabriken KG) and tested according to the example of offset ink.

Table 4

Result of the test in a gravure ink when incorporated as micropowder

The waxes according to the invention bring about a smaller color difference and thus improved abrasion resistance. Surprisingly, there has also been one Lower sliding friction with addition of sorbitan esters shown.

3) Flexographic printing ink

The mixtures M3, M4, M5, M6, M7, M8, M11 and M12 were incorporated at 1% by weight into an aqueous flexographic printing ink with intensive stirring using a dissolver. The flexographic printing ink is composed of 35% by weight of Synthacryl® SW 175, 20% by weight of Hostapermblau® B2 G, 45% by weight of water. The ink was made with a wire doctor blade with a wet film thickness of 6 µm on Allgäu 80 g / m 2 paper (G. Haindl'sche Papierfabriken KG) and tested according to the example of offset ink.

Table 5

Result of the test in a flexographic printing ink when incorporated as micropowder

The waxes according to the invention bring about a smaller color difference and thus improved abrasion resistance. Surprisingly, there has also been one Lower sliding friction with addition of sorbitan esters shown.

Claims (8)

1. Use of mixtures of
  • a) polyolefin waxes from C 2 -C 18 -α-olefins, produced using metallocene catalysts, with one or more further additives selected from the group consisting of
  • b) polytetrafluoroethylene,
  • c) amide waxes,
  • d) montan waxes including acid and ester waxes with a carbon chain length of the carboxylic acid from C 22 to C 36 ,
  • e) natural plant waxes,
  • f) reaction products of sorbitol (sorbitol) with saturated and / or unsaturated fatty acids and / or montanic acids,
  • g) synthetic hydrocarbons,
  • h) paraffins and microcrystalline waxes, which are obtained from petroleum refining
  • i) polar polyolefin waxes, producible by oxidation of ethylene or propylene homopolymer and copolymer waxes or their grafting with maleic anhydride
for the production of printing inks.
2. Use according to claim 1, wherein component a) is an ethylene homo- or Is copolymer wax.
3. Use according to claim 1, wherein component a) is a propylene homo- or Is copolymer wax.
4. Use according to one or more of claims 1 to 3, wherein the Polyolefin waxes of component a) a molecular weight distribution Mw / Mn <5 exhibit.
5. Use according to one or more of claims 1 to 4, wherein the Polyolefin waxes have a melt viscosity of 5 to 100,000 mPas.  
6. Use according to one or more of claims 1 to 5, wherein the Polyolefin waxes have a dropping point of 70 to 165 ° C.
7. Use according to one or more of claims 1 to 6, wherein the Proportion of the additive (s) 1-99% by weight based on the Total mass of the mixture is.
8. Use according to one or more of claims 1 to 7, wherein the Waxes can be used in micronized form.
DE10009754A 2000-03-01 2000-03-01 Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion Withdrawn DE10009754A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE10009754A DE10009754A1 (en) 2000-03-01 2000-03-01 Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
DE10009754A DE10009754A1 (en) 2000-03-01 2000-03-01 Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion
DE2001508749 DE50108749D1 (en) 2000-03-01 2001-02-15 Use of polyolefin waxes manufactured by means of metal cell calculators for the manufacture of printing colors
JP2001564290A JP2003525339A (en) 2000-03-01 2001-02-15 Wax for printing ink production
PCT/EP2001/001667 WO2001064799A1 (en) 2000-03-01 2001-02-15 Waxes for producing printing inks
EP20010909755 EP1272575B8 (en) 2000-03-01 2001-02-15 Use of polyolefin waxes obtained with metallocene catalysts for producing printing inks
CN 01805871 CN1406267A (en) 2000-03-01 2001-02-15 Waves for producing printing inks
ES01909755T ES2256205T3 (en) 2000-03-01 2001-02-15 Use of prepared polyolefin waxes by metalocene type catalysts for the production of printing inks.
US10/220,411 US7521490B2 (en) 2000-03-01 2001-02-15 Waxes for producing printing inks

Publications (1)

Publication Number Publication Date
DE10009754A1 true DE10009754A1 (en) 2001-09-13

Family

ID=7632963

Family Applications (1)

Application Number Title Priority Date Filing Date
DE10009754A Withdrawn DE10009754A1 (en) 2000-03-01 2000-03-01 Printing ink containing olefin polymer produced using metallocene catalyst and additives, useful in offset, intaglio of flexographic printing, has high resistance to abrasion

Country Status (1)

Country Link
DE (1) DE10009754A1 (en)

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