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WO1996034921A1 - Solvant exempt d'huiles minerales pour encres d'imprimerie a base d'ether - Google Patents

Solvant exempt d'huiles minerales pour encres d'imprimerie a base d'ether Download PDF

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Publication number
WO1996034921A1
WO1996034921A1 PCT/EP1996/001771 EP9601771W WO9634921A1 WO 1996034921 A1 WO1996034921 A1 WO 1996034921A1 EP 9601771 W EP9601771 W EP 9601771W WO 9634921 A1 WO9634921 A1 WO 9634921A1
Authority
WO
WIPO (PCT)
Prior art keywords
dialkyl ethers
ether
printing inks
fatty acid
printing
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.)
Ceased
Application number
PCT/EP1996/001771
Other languages
German (de)
English (en)
Inventor
Matthias Fies
Dieter Feustel
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AU56929/96A priority Critical patent/AU5692996A/en
Publication of WO1996034921A1 publication Critical patent/WO1996034921A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent

Definitions

  • the invention relates to the use of dialkyl ethers, optionally in a mixture with fatty acid esters, as a substitute for mineral oils in solvents for printing inks.
  • the invention further relates to printing inks which contain binders, pigments and solvents containing dialkyl ethers and, if appropriate, fatty acid esters and, if appropriate, further additives.
  • the printing ink is transferred from the hard, raised letters, which are covered with a thin layer of ink to rubber rollers, to the substrate.
  • the printing ink must be such that it dries relatively slowly and does not start to harden prematurely.
  • fast-moving Newspaper printing machines using the rotary high-pressure process require viscous, very slow-drying printing inks.
  • the shape to be imaged is fixed on the printing plates in the form of zones of opposite polarity.
  • the hydrophobic, viscous ink only wets the likewise hydrophobic areas on the printing plates.
  • the motif is engraved on the printing plate. After wetting the printing plate with the relatively thin liquid printing ink, the surface is stripped off and only printing ink remains in the engraved depressions, from which it is then transferred to the substrate to be printed.
  • the previous examples show that printing inks have to meet a variety of requirements against the background of economy.
  • the main components of an ink are pigments, binders, solvents and additives, with which the desired properties of the inks are adjusted.
  • the viscosity, flow behavior and stickiness can be adjusted.
  • it must be able to be compatible with a wide variety of binders and a wide variety of additives; on the other hand, it should be able to adjust the viscosity in the desired range.
  • the aim of the present invention is to substitute mineral oil in solvent mixtures used for the production of printing inks by substances which are at least equally effective in terms of effectiveness but clearly superior in environmental compatibility.
  • linear dialkyl ethers optionally in a mixture with fatty acid esters, can completely replace mineral oils as solvents for printing inks in the most varied of fields of use
  • solvent in the context of the present invention stands both for an agent for producing real solutions and for a medium in which the ingredients can be present, for example, as a stable suspension, dispersion, emulsion, gel and / or mixture of these physically different states.
  • solvent is used in the following text, even if, for example, a suspension or a gel is present.
  • the invention relates to the use of dialkyl ethers with a total of 6 to 72 carbon atoms as solvents for the production of printing inks.
  • Those dialkyl ethers which contain a total of between 12 and 36 carbon atoms are preferably used. In a particularly preferred embodiment, those dialkyl ethers are used which have a total of between 12 and 24 carbon atoms.
  • dialkyl ethers used according to the invention preferably contain only one ether group.
  • both symmetrical and asymmetrical dialkyl ethers can be used.
  • Symmetrical linear dialkyl ethers are, for example, di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n-undecyl ether and di-n-dodecyl ether. Further symmetrical, linear dialkyl ethers are revealed to the person skilled in the art by linking the ends of two identical alkyl radicals from the homologous series of the n-alkanes via an oxygen atom.
  • asymmetrical dialkyl ethers can also be used.
  • Unsymmetrical ethers are characterized in that the alkyl residues of the dialkyl ether are different in pairs. These include, for example, the n-hexyl-n-octyl ether, n-octyl-n-decyl ether, n-decyl-n-undecyl ether, n-undecyl-n-dodecyl ether and the n-hexyl-n-undecyl ether.
  • dialkyl radicals of the dialkyl ethers can not only be linear and identical or different in pairs, dialkyl ethers whose alkyl radicals have one or more branches can also be used according to the invention exhibit. It is irrelevant whether the branches appear in one or both alkyl residues.
  • Symmetrical dialkyl ethers with branched alkyl radicals are, for example, di-tert-butyl ether, di-isopentyl ether, di-3-ethyldecyl ether.
  • asymmetrical dialkyl ethers with the structure mentioned here are tert-butyl-n-octyl ether, isopentyl-n-octyl ether or 2-methyl-pentyl-n-octyl ether.
  • Further homologs are accessible to the person skilled in the art knowing the homologous series of the branched paraffins by linking two identical or different, branched alkyl radicals at the same end via an oxygen atom.
  • the ethers used according to the invention can also have double bonds in the alkyl chain.
  • the number of double bonds is not limited here and they can be in the conjugated or in the isolated position.
  • Symmetrical dialkyl ethers of the form described are, for example, di-hexenyl ether, di-octenyl ether, di-decenyl ether, di-undecenyl ether and di-octadecenyl ether.
  • unsymmetrical, unsaturated dialkyl ethers are vinyl-n-octyl ether, allyl-n-octyl ether, but-2-enyl-dodecyl ether, oct-3-enyl-n-octyl ether and all other homologues and isomers with 6 to 72 C atoms , which result to the person skilled in the art in a manner known per se from the combination of the corresponding alkenyl radicals on an oxygen atom.
  • dialkyl ethers can also be used according to the invention which have a combination of features such as e.g. symmetrical, branched, unsaturated or unsymmetrical consisting of a linear, saturated and a branched unsaturated alkyl chain:
  • dialkyl ethers which are prepared in a manner known per se from fatty alcohols having 6 to 12 carbon atoms.
  • the fatty alcohols from the C 8 and Cio fatty acids which are obtained from the saponification of palm kernel oil, coconut oil and cuphea oil, are particularly noteworthy.
  • the dialkyl ethers described so far can be used as solvents for the production of printing inks both in pure form and in a mixture with one another and with other substances.
  • a mixture of di-n-octyl ether and di-n-decyl ether can be used according to the invention.
  • the mixing ratio of the dialkyl ethers to one another does not matter.
  • Examples of mixing ratios of two dialkyl ethers would be 50:50, 40:60, 30:70, 20:80, 10:90 and the possible intermediates, the sum of the proportions of both ethers always giving 100.
  • Ternary and higher mixtures in particular those resulting from the condensation of reduction products of natural fats and oils, can also be used according to the invention.
  • the best mixing ratio for the printing ink to be produced can be determined by a person skilled in the art on the basis of a few experiments.
  • di-n-octyl ether and di-n-decyl ether are particularly suitable for use in the present invention.
  • dialkyl ethers are used in a mixture with fatty acid esters with 8 to 72 carbon atoms.
  • the esters are in a range from 1 to 90% by weight. % used based on the total solvent content.
  • fatty acid esters whose fatty acid residue is of natural origin are preferably used.
  • those fatty acid esters can also be used which contain one or more double bonds in the fatty acid residue.
  • Particularly preferred are the unsaturated fatty acids and among them the naturally occurring ones, such as oleic acid, erucic acid, ricinoleic acid, tall oil fatty acid, linoleic acid, azelaic acid, of which in turn those with 8 to 18 carbon atoms are particularly preferred.
  • Fatty acid esters which can be obtained by transesterification of naturally occurring triglycerides such as beef tallow, coconut oil, palm oil, palm kernel oil, rapeseed oil, cottonseed oil, soybean oil, sunflower oil and linseed oil with corresponding alcohols and thus represent a mixture of fatty acid esters with different fatty acid residues can also be used according to the invention.
  • naturally occurring triglycerides such as beef tallow, coconut oil, palm oil, palm kernel oil, rapeseed oil, cottonseed oil, soybean oil, sunflower oil and linseed oil with corresponding alcohols and thus represent a mixture of fatty acid esters with different fatty acid residues
  • Saturated or unsaturated fatty acid esters whose acid residue is a derivative of the acid residue of a naturally occurring fatty acid can also be used according to the invention.
  • the esters of ricinenic acid, pelargonic acid and elaidic acid can be used according to the invention.
  • the esters of the dicarboxylic acids resulting from the dimerization of naturally occurring fatty acids are also suitable.
  • the alcohol components of the fatty acid esters can consist of linear or branched, monofunctional or polyfunctional alcohols with 1-36 C atoms.
  • the alcohol components of the fatty acid esters can be saturated or unsaturated with one or more double bonds.
  • All mono-, di- and trifunctional alcohols are particularly suitable according to the invention. These include, in particular, the straight-chain and branched alkanols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, hexanol and the higher homologues.
  • unsaturated alcohols such as allyl alcohol, butenyl alcohol, pentenyl alcohol and the higher homologues up to the fatty alcohols such as oleyl alcohol and erucalcohol as well as the diols obtainable from the reduction of dimer fatty acids can also be used according to the invention.
  • the use of monofunctional alcohols with 1 to 6 is preferred C atoms, especially the use of monofunctional alcohols with 1 - 4 C atoms.
  • a preferred embodiment of the invention is present if the dialkyl ether or the mixture used of dialkylethers and Fettklareestern at 20 ° C and preferably at 15 C ⁇ are liquid. If a mixture of dialkyl ethers and fatty acid esters is used, the state of matter of the individual components at the desired temperature does not matter as long as the mixture is liquid.
  • the viscosities of the printing inks produced can be adjusted over a wide range.
  • the optimal mix is based on many different parameters such as Printing process, substrate to be printed, processing temperature, binder, pigment and additives.
  • the optimum ratio of the components in each case can easily be determined by the average person skilled in the art on the basis of a few experiments.
  • Another object of the invention is a printing ink which contains binders, pigments and solvents containing dialkyl ethers having 6 to 72 carbon atoms and preferably only one ether group.
  • It may contain other ingredients such as surfactants, fillers, stabilizers, siccatives and rheology improvers.
  • Resins known per se such as, for example, shellac, rosin, phenol-modified rosin, polyamides, phenolic resins, polyurethanes, polyepoxides, cellulose, nitrocellulose and preferably alkyd resins, can be used as binders.
  • solvent or solvent mixture according to the invention offset, transfer, flat, high-pressure and / or gravure inks can be produced with the addition of the customary components.
  • Example 1 Production of a gravure ink
  • a pigment base (Hacolor PY 13)) together with 100 parts of a commercially available, drying alkyd resin based on soybean oil (isophthalic acid, t methylolpropane, 1500 dPa • s, 20 ° C), 10 parts of cobalt octoate with a cobalt content of 6% , 20 parts of a micronized polyethylene wax, 320 parts of a phenol-modified rosin and 440 parts of a mixture of 45% 2-ethylhexyl coconut fatty acid, 45% propyl oleic acid and 10% di-n-decyl ether are rubbed on a three-roll mill.
  • composition instead of 440 parts of a mixture of 45% coconut fatty acid 2-ethylhexyl ester, 45% oleic acid propyl ester and 10% di-n-decyl ether, 440 parts of a mineral oil with an aromatic content of 18% (boiling range 270 - 310 ° C, aniline point 72 ° C) is used.
  • the colors were subjected to a printing comparison.
  • the applied ink layer was 1.5 g / m 2 ⁇ 5% in all cases.
  • furnace black 100 parts of furnace black were mixed with 10 parts of a micronized polyethylene wax, 35 parts of a commercially available drying alkyd resin based on soybean oil (isophthalic acid, trimethylolpropane, 1500 dPa • s, 20 ° C.), 2 parts Cobalt octoate with a cobalt content of 6%, 65 parts of a phenol-modified rosin, 50 parts of Gilsonite asphalt and 240 parts of di-octyl ether (boiling range 286 ° C.) melted together at 200 ° C. and rubbed on a three-roll mill.
  • composition 240 parts of a mineral oil having an aromatic content of 18% was used instead of 240 parts of dioctyl ether (boiling range 270-310 ° C, aniline point 72 ⁇ C). The components were melted together at 200 ° C. and rubbed on a three-roll mill.
  • the colors were printed on newsprint (52 g / m 2 ) using rotary printing and subjected to a printing comparison.
  • the applied ink layer was 1.5 g / m 2 ⁇ 5% in all cases.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne la production d'encres d'imprimerie exemptes d'huiles minérales qui se caractérisent en ce que le solvant utilisé contient du dialkyléther avec 6 à 72 atomes de carbone et le cas échéant des esters d'acides gras. L'invention concerne également des encres d'imprimerie qui contiennent des liants, des pigments et des solvants contenant du dialkyléther et le cas échéant, des esters d'acides gras, et éventuellement d'autres additifs.
PCT/EP1996/001771 1995-05-04 1996-04-26 Solvant exempt d'huiles minerales pour encres d'imprimerie a base d'ether Ceased WO1996034921A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU56929/96A AU5692996A (en) 1995-05-04 1996-04-26 Mineral oil-free solvent for ether-based printing inks

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19516027.4 1995-05-04
DE19516027A DE19516027A1 (de) 1995-05-04 1995-05-04 Mineralölfreie Lösungsmittel für Druckfarben auf Etherbasis

Publications (1)

Publication Number Publication Date
WO1996034921A1 true WO1996034921A1 (fr) 1996-11-07

Family

ID=7760840

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/001771 Ceased WO1996034921A1 (fr) 1995-05-04 1996-04-26 Solvant exempt d'huiles minerales pour encres d'imprimerie a base d'ether

Country Status (3)

Country Link
AU (1) AU5692996A (fr)
DE (1) DE19516027A1 (fr)
WO (1) WO1996034921A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005060693A (ja) * 2003-07-30 2005-03-10 The Inctec Inc インキ

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB371202A (en) * 1931-04-02 1932-04-21 Wacker Chemie Gmbh Improvements relating to printing colours
US2079229A (en) * 1932-06-30 1937-05-04 Unichem Chemikalien Handels A Pigment paste for carbon papers, typewriter ribbons, and stencil sheets
US4566907A (en) * 1984-02-14 1986-01-28 Mitsubishi Paper Mills, Ltd. Color-developing ink for non-carbon copying paper

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB371202A (en) * 1931-04-02 1932-04-21 Wacker Chemie Gmbh Improvements relating to printing colours
US2079229A (en) * 1932-06-30 1937-05-04 Unichem Chemikalien Handels A Pigment paste for carbon papers, typewriter ribbons, and stencil sheets
US4566907A (en) * 1984-02-14 1986-01-28 Mitsubishi Paper Mills, Ltd. Color-developing ink for non-carbon copying paper

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005060693A (ja) * 2003-07-30 2005-03-10 The Inctec Inc インキ

Also Published As

Publication number Publication date
AU5692996A (en) 1996-11-21
DE19516027A1 (de) 1996-11-07

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