EP0280650A1 - Utilisation de dérivés déterminés de benztriazole comme agents de protection contre la lumière pour matériaux d'enregistrement pour impression à projection d'encre - Google Patents
Utilisation de dérivés déterminés de benztriazole comme agents de protection contre la lumière pour matériaux d'enregistrement pour impression à projection d'encre Download PDFInfo
- Publication number
- EP0280650A1 EP0280650A1 EP88810092A EP88810092A EP0280650A1 EP 0280650 A1 EP0280650 A1 EP 0280650A1 EP 88810092 A EP88810092 A EP 88810092A EP 88810092 A EP88810092 A EP 88810092A EP 0280650 A1 EP0280650 A1 EP 0280650A1
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- EP
- European Patent Office
- Prior art keywords
- formula
- alkyl
- group
- alkylene
- compounds
- 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.)
- Granted
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- 0 CO*(****1)*1O Chemical compound CO*(****1)*1O 0.000 description 2
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5227—Macromolecular coatings characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants
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- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
Definitions
- the invention relates to the use of certain UV absorbers of the 2- (2-hydroxyphenyl) benzotriazole type as light stabilizers for recording materials for ink-jet printing and to the recording materials stabilized by means of these compounds against light damage.
- Inkjet printing is a very fast printing process that can be controlled by electrical signals.
- a fine jet of ink droplets is sprayed through a nozzle onto the recording material.
- the ink is a solution of a dye in an aqueous or non-aqueous solvent.
- the recording material should quickly and permanently absorb the dye of the ink.
- specially prepared papers or plastic foils are used, which are coated with a dye-binding layer.
- pigments are rarely used, but mainly dyes that are completely dissolved in the inkjet medium.
- these dyes generally have a lower light fastness than the color pigments common in conventional printing inks.
- records made in inkjet printing can only be stored for a limited period under the influence of light. When stored in the light for a long time, they begin to fade or change color.
- R as C 1 -C 12 alkyl can, for example, methyl, ethyl, isopropyl, n-butyl, tert-butyl, sec-butyl, tert-pentyl, sec-pentyl, n-hexyl, sec.hexyl, n-octyl .Octyl, sec.Decyl or n-dodecyl.
- R as cycloalkyl can in particular be cyclohexyl.
- R as phenylalkyl can in particular be a, a-dimethylbenzyl.
- R is preferably a branched alkyl radical, in particular tert-butyl.
- R 1 as C i -C 4 alkyl or alkoxy can be, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methoxy, ethoxy, isopropoxy, butoxy or tert-butoxy.
- R 4 , R 5 , R 7 and R 10 as C 1 -C 18 alkyl can be unbranched or branched alkyl, such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, 2-ethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, 1,1,3,3-tetraethylbutyl, n-decyl, isodecyl, n-dodecyl, 1,1,7, 7-tetramethyloctyl, n-tetradecyl or n-octadecyl.
- alkyl such as, for example, methyl, ethyl, propyl, isopropyl
- R 3 as alkyl substituted by -OH or -OCOR 10 can, for example, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, 2,3-dihydroxypropyl, 2,2-di (hydroxymethyl) propyl, 4-hydroxybutyl , 6-hydroxyhexyl, 8-hydroxyoctyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-octanoyloxypropyl, 2,3-diacetyloxypropyl or 4-acetoxybutyl.
- R 3 , R 4 , R 5 as C 3 -C 30 alkyl interrupted by -O- or -N (R 7 ) - can, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 2-isopropoxyethyl, 2-octyloxyethyl , 3,6-dioxaheptyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 5-hydroxy-3-oxapentyl or 11-hydroxy-3,6,9-trioxaundecyl.
- R 4 and R 5 as C 1 -C 4 hydroxyalkyl can be, for example, hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl or 2-hydroxybutyl.
- R 4 and R 5 as C 5 -C 12 cycloalkyl can be, for example, cyclopentyl, cyclohexyl, methylcyclohexyl, cyclooctyl or cyclododecyl.
- R 3 can also be cycloalkyl substituted by OH, for example 4-hydroxycyclohexyl.
- R 3 as C 2 -C 18 alkenyl, which can be substituted by OH, can be, for example, vinyl, allyl, methallyl, 2-butenyl-1, oleyl or 4-hydroxy-2-butenyl-1.
- R 4 and R 5 as C 3 -C 8 alkenyl can in particular be allyl.
- R 3 , R 4 and R 5 as C 7 -C 15 phenylalkyl or alkylphenylalkyl can be, for example, benzyl, 2-phenylethyl, 1-phenylethyl, 3-phenylpropyl, 2-phenylpropyl-2, 4-methylbenzyl or 4-octylbenzyl.
- R 4 and R 5 as phenyl substituted by alkyl, alkoxy or halogen can be, for example, 4-tolyl, 4-isopropylphenyl, 3-methoxyphenyl, 4-ethoxyphenyl, 4-fluorophenyl or 4-chlorophenyl.
- R 6 and R 9 as C 2 -C 8 alkylene can be branched or straight-chain alkylene, such as, for example, 1,2-ethylene, tri-, tetra-, penta-, hexa- or octamethylene, 2,2-dimethyl-1, 3-propylene, 1,2-propylene or 1,2-butylene.
- R 8 as C 2 -C 12 alkylene can also be, for example, deca- or dodecamethylene.
- R 6 as alkenylene or alkynylene can be, for example, 2-butenylene-1,4, 2-butynylene-1,4 or 2-methyl-2-butenylene-1,4.
- R 6 and R 9 as alkylene interrupted by -0- or -N (R 7 ) - can, for example, 3-oxapentylene-1,5, 3,6-dioxaoctylene-1,8, 3,6,9-trioxaundecylene-1, 11, 3- (Methylaza) -pentylene-1,5 or 3,9-Dioxa-5- (methyla-za) -undecylene-1,11.
- R 11 as alkanetriyl radical can be, for example, propane-1,2,3-triyl or a radical CH 3 C (CH 2 -) 3 or C 2 H 5 C (CH 2 -) 3 .
- R 12 as alkane tetrayl radical can be, for example, butane-1,2,3,4-tetrayl or a radical C (CH 2- ) 4 .
- the compounds of the formula are carboxylic acids, carboxylic esters or carboxamides.
- the esters are particularly suitable, in particular the compounds of the formula I, in which n is 1 or 2 and R 2 is a group -OR 3 or -OR 6- O-.
- Mixtures of several compounds of the formula are often obtained in the preparation of these compounds.
- the esterification of a diol can produce the monoester alongside the diester.
- Polyalkylene glycols are often technical mixtures with different degrees of oxyalkylation. If such diols are used, corresponding mixtures of compounds of the formula 1 are obtained.
- Such mixtures can be used for the use according to the invention as well as uniform compounds. Since such mixtures are mostly liquid, they can even be of particular advantage.
- Examples of these are the compounds 8), 20), 21), 23), 28), 34), 47) and 51) listed above or mixtures of 3) and 24), of 19) and 29), of 33) and 46) or from 5), 26), 33) and 46).
- New compounds and as such also the subject of the invention are the compounds of formula II, wherein R and R 3 have the meanings given above.
- the benzotriazoles used according to the invention are distinguished by an increased hydrophilicity.
- hydrophilic UV absorbers would be particularly suitable as light stabilizers for inkjet printing recording materials.
- the effect of the UV absorbers consists in filtering out the short-wave light (200-400 nm) and this effect should only depend on the wavelength range of the light absorption of the molecule, but should be independent of other properties of the molecule.
- the high effectiveness of the UV absorbers according to the invention was surprising.
- the compounds of formula I can be dispersed well.
- the recording material is a two-dimensional sheet which can consist of one or more layers.
- the carrier layer usually consists of paper or a plastic film or a laminate of such materials.
- the carrier layer can be coated on one or both sides with a material which is particularly receptive to the ink dyes.
- the recording material can be transparent, for example in the case of projection foils. In most cases, however, the recording material is not transparent and is read by the supervisor.
- the UV absorber according to the invention can already be incorporated into the carrier material during the production thereof, for example in the production of paper by adding it to the paper pulp, or in the production of plastic films by adding it to the polymer before extrusion.
- a second method of application is spraying the carrier material with a solution of the UV absorber in a volatile solvent.
- a dye-affine layer is applied to the carrier material and in this case the UV absorber according to the invention is added to the coating material.
- These coating compositions usually consist of a solid filler and a binder, as well as smaller proportions of additives.
- the filler is the main quantitative component of the coating composition.
- Examples of common fillers are lime, chalk, silica, kaolin, talc, clay, calcium, magnesium or aluminum silicates, gypsum, barite, zeolite, bentonite, diatomaceous earth, vermiculite, titanium dioxide, zinc oxide, magnesium oxide, magnesium carbonate, starch or the surface-modified silica described in JP-A-85/260 377.
- the binder binds the filler to itself and to the carrier material. It can be used as an aqueous solution, organic solution or aqueous dispersion.
- binders are Polyvinyl alcohol, partially hydrolyzed polyvinyl acetate, cellulose ether, polyvinyl pyrrolidone and its copolymers, polyethylene oxide, salts of polyacrylic acid, sodium alginate, oxidized starch, gelatin, casein, vegetable rubber, dextrin, albumin, dispersions of polyacrylates or acrylate-methacrylate copolymers, latices of natural or synthetic rubber, poly (meth) acrylamide, polyvinyl ether, polyvinyl ester, copolymers of maleic acid, melamine resins, urea resins or chemically modified polyvinyl alcohols, as described in JP-A-86/134 290 or 86/134 291.
- a dye receptor or mordant can be added to the binder, which fix the dye more firmly to the coating.
- Dye receptors for acid dyes are cationic or amphoteric in nature.
- cationic receptors are polymeric ammonium compounds such as e.g. Polyvinylbenzyl-trimethylammonium chloride, polydiallyl-dimethylammonium chloride, polymethacryloxyethyl-dimethyl-hydroxyethylammonium chloride, polyvinylbenzylmethylimidazolium chloride, polyvinylbenzyl-picolinium chloride or polyvinylbenzyl-tributylammonium chloride.
- the dye-binding coating can contain a number of other additives, such as e.g. Antioxidants, light stabilizers (including UV absorbers that do not belong to the UV absorbers according to the invention), viscosity improvers, optical brighteners, biocides or / and antistatic agents.
- Antioxidants e.g. Antioxidants, light stabilizers (including UV absorbers that do not belong to the UV absorbers according to the invention), viscosity improvers, optical brighteners, biocides or / and antistatic agents.
- antioxidants are, in particular, sterically hindered phenols and hydroquinones, e.g. the antioxidants listed in GB-A-2 088 777, or JP-A-85/72 785, 85/72 786 and 85/71 796.
- suitable light stabilizers are in particular organic nickel compounds and sterically hindered amines, such as e.g. those in JP-A-83/152 072, 86/146 591, 86/163 886, 85/72 785 and 86/146 591 or that in GB-A-2 088 777, JP-A-84/169 883 and 86/177 279 mentioned light stabilizers.
- the UV absorber used according to the invention is a liquid
- these additives can be dissolved directly in the UV absorber. Or they are pre-dissolved in an organic solvent and mixed with the liquid UV absorber or with a solution of the UV absorber in an organic solvent.
- Aqueous coating compositions are preferably used. In this case, the UV absorber and the other additives must be dispersed as homogeneously as possible in the coating composition.
- the UV absorber is liquid, it can be dispersed directly in the binder or in the coating composition after the addition of surface-active agents. If the UV absorber is solid or viscous, it is advisable to dissolve it in an organic solvent and to disperse this solution in the coating material.
- the solvent used is preferably a low-volatility solvent so that the UV absorber remains in the liquid state even after the recording material has been stored for a long time.
- a volatile auxiliary solvent is usually added, which is removed again during the production process of the recording material.
- low volatility solvents are organic liquids with an oily character and high boiling point, e.g. Phthalic acid esters (e.g. dimethyl, diethyl, dibutyl, diamyl, dihexyl, diheptyl, dioctyl, dinonyl or didecyl phthalate, or dibutyl chlorophthalate), glycolic acid esters (e.g.
- butyl phthalyl butyl glycolate phenols (e.g. 2,4-di-n -amylphenol, 2,4-di-tert.amyiphenoi), phosphoric acid esters (e.g. diphenyl, triphenyl, tricresyl, cresyl diphenyl, dioctyl, dioctyl butyl, trioctyl, tridecyl, trixylenyl, tri ( isopropylphenyl), tributyl, trihexyl, trinonyl, trioleyl or tri (butoxyethyl) phosphate, citric acid esters (for example O-acetyl-triethyl-, -tributyl-, -trihexyl-, -trioctyl-, -trinonyl- or -tridecyl citrate), benzoic acid esters (e.g.
- esters of substituted benzoic acids e.g.
- butyl 2-methoxybenzoate pentyl-o-methylbenzoate, decyl-p-methylbenzoate, lauryl-o-chlorobenzoate, propyl-24, -dichlorobenzoate, oleyl-2,4-dichlorobenzoate or octyl-n-methoxybenzoate
- fatty acid esters and dicarboxylic acid ureester e.g. Hexadecyl myristate, dibutyl sebacate, dibutoxyethyl succinate, dioctyl adipate, dioctyl azelate, benzyl caprylate
- esters of polyols e.g.
- glycerol trialkyl ether glycerol 1,3-dialkyl ether, n-pentadecylphenyl ether or 3-pentadecylphenyl ethyl ether
- Alkyl aryl carbamates eg ethyl-N, N-diphenyl-carbamate
- Liquids not boiling above 150 ° C can be used as volatile solvents.
- these are lower alkyl acetates or propionates (eg methyl, ethyl, n-propyl, isopropyl, butyl acetate, methyl or ethyl propionate), ethyl formate, diethyl carbonate, lower chloroalkanes (eg carbon tetrachloride, di- and trichlorethylene, 1,2-dichloropropane, chloroform or amyl chloride), ketones (e.g. acetone, methyl ethyl ketone, diethyl ketone or methyl isobutyl ketone), ethers (e.g.
- diisopropyl ether dibutyl ether, tetrahydrofuran, dioxane
- alcohols e.g. methanol, ethanol, Isopropanol, butanol
- monoethers of diols e.g. ethylene glycol monomethyl ether or monoethyl ether
- hydrocarbons e.g.
- cyclohexane methylcyclohexane, ligroin, benzene, toluene, xylene
- nitromethane acetonitrile
- dimethyl sulfoxide N-methylpyrrolidone
- dimethylformamide Tetrahydrothiophene dioxide
- butyrolactone 1,2-dimethoxyethane
- auxiliary solvents serve to better disperse the UV absorber or its solution in high-boiling solvent.
- the UV absorber is a liquid of low viscosity which can be dispersed well owing to its polar or hydrophilic character, no solvent is necessary, which is the case with many of the UV absorbers used according to the invention. This can simplify the preparation of the emulsions, and there is no need to recover the auxiliary solvent.
- auxiliary solvent it must be removed before the coating process. This can be done by heating and / or vacuum treatment, e.g. in a vacuum spray evaporator or a vacuum rotary evaporator.
- the binder of the coating composition is an aqueous solution, a dispersion or a latex
- the oily phase of the UV absorber or its solution must be dispersed homogeneously in the aqueous phase and this dispersion should have a pot life as long as possible during which the dispersed Do not enlarge oil droplets or the dispersion segregates.
- This is possible - apart from the use of solvents - by using surface-active agents, by adding colloids to the aqueous phase and by correspondingly intensive mixing and dispersing machines.
- suitable dispersing machines are ultrasound devices, turbo stirrers, homogenizers, colloid mills, bead mills, sand mills or high-speed stirrers.
- colloids which are added to the aqueous phase and stabilize the dispersions formed are polyvinyl alcohol, cellulose ether, polyethylene oxide, salts of polyacrylic acid, gelatin, vegetable gums, dextrin, casein or albumin. These colloids are also binders.
- surface-active dispersing aids can be nonionic, amphoteric, anionic or cationic surfactants.
- nonionic surfactants are esters or ethers of polyethylene oxides or polypropylene oxides or of their copolymers, fatty acid alkanolamides, ethoxylated alkanolamides, partial fatty acid esters of polyols (for example of glycerol, polyglycerol, sorbitol, pentaerythritol or sucrose), N-alkylmorpholines or long-chain amine oxides .
- amphoteric surfactants are fatty acid amidoalkyl betaine, fatty acid amidoalkyl sultaine, fatty acid imidazoline betalne, N-alkyl-ß-aminopropionic acids or alkylene bis (amidoalkylglyclnate).
- anionic surfactants are alkali or ammonium salts of fatty acids, of alkyl sulfates, of amido ethylene oxide sulfates, of alkyl or alkylaryl sulfonic acids, of N-alkyl and N-acyl-taurines, of fatty acid isethionates, of alkyl sulfosuccinates, of lignin sulfonates, of petroleum sulfonates, of mono- or dialkyl phosphates, of N-alkyl sarcosines, of alkyl sulfonamidoacetic acids, of alkyl lactates, of monoalkyl succinates, of fatty acid-protein condensation products, of (alkyl) naphthenic acids, of abietic acids, of sulfonated fatty acids or of N-acyl aminocarboxylic acids.
- cationic surfactants are the quaternary ammonium salts of long-chain fatty amines and benzylamines, imidazolinium, pyridinium, picolinium or morpholinium salts with long-chain alkyl radicals, quaternary ammonium salts of long-chain alkylamidoalkylamines or bis-ammonium salts of quaternary diamines.
- the surfactant can be pre-dissolved in the oil phase or in the water phase or in both phases. Different surfactants can also be added in both phases, but these must not have opposite activity (cationic-anionic).
- the oil-in-water dispersion can be destroyed when the filler is added if the surface of the filler has an electronegative charge, e.g. can be the case with silica.
- This problem can be solved by pretreating the surface of the filler.
- silanes with functional groups are used that modify the surface's electrical charge accordingly, e.g. 3- (trimethoxysllyl) propyl-dimethyl-octadecyl-ammonium chloride.
- alkylarylsulfonates can be increased by adding wetting agents, which are also surfactants.
- wetting agents include sodium dloctyl sulfosuccinate and alkylnaphthalene sulfonates.
- the binder of the coating composition is applied as a solution in an organic solvent, the UV absorber and the other additives need not be dispersed. They are then added directly to the binder solution or previously dissolved in an organic solvent.
- the coating composition is applied to the carrier, which is usually a paper, and dried by heating.
- the recording material thus prepared preferably contains 1 to 5000 mg / m 2 , in particular 200-1200 mg / m 2, of the UV absorber.
- the recording material prepared in this way which contains at least one of the UV absorbers according to the invention in its surface layer and which can contain the other additives mentioned, is likewise a subject of the invention.
- This recording material not only has a good absorption capacity for inkjet dyes, it also gives the printed dye a high light fastness. It does not matter what type of ink and the dye dissolved in it and what type of printer device is used.
- the inks are mostly aqueous inks, but they can also be solutions of the dye in an organic solvent or in a molten wax.
- Aqueous inks usually contain highly water-soluble solvents, e.g. Mono-, di-, tri- or higher ethylene glycols, propylene glycol, 1,4-butanediol or ethers of such glycols, thiodiglycol, glycerol and its ethers and esters, polyglycerol, mono-, di- and triethanolamine, propanolamine, dimethylformamide, dimethyl sulfoxide, dimethylacetamide , N-methylpyrrolidone, 1,3-dimethylimidazolidone, methanol, ethanol, isopropanol, n-propanol, diacetone alcohol, acetone, methyl ethyl ketone or propylene carbonate.
- highly water-soluble solvents e.g. Mono-, di-, tri- or
- Aqueous inks contain water-soluble dyes, which are also known for dyeing natural fibers. This can e.g. Monoazo, bisazo or polyazo or phthalocyanine dyes. Examples include Food Black 2, C.I. Direct Black 19, C.1. Sulfur Black 1, Acid Red 35, Acid Yellow 23 or copper phthalocyanines.
- Aqueous inks can also contain various additives in smaller amounts, e.g. Binders, surfactants, biocides, corrosion inhibitors, sequestering agents, pH buffers or conductivity additives. They can also contain water-soluble UV absorbers or other water-soluble light stabilizers. In general, however, the addition of a UV absorber according to the invention to the recording material is sufficient.
- the ink is a non-aqueous ink, it represents a solution of the dye in an organic solvent or solvent mixture or in a molten wax.
- solvents used for this are alkyl carbitols, alkyl cellosolves, dialkylformamides, dialkylacetamides, alcohols, especially alcohols with 1 -4 C atoms, acetone, methyl ethyl ketone.
- solid waxes as solvents are stearic or palmitic acid.
- solvent-based inks contain soluble dyes therein, e.g. Solvent Red, Solvent Yellow, Solvent Orange, Solvent Blue, Solvent Green, Solvent Violet, Solvent Brown or Solvent Black.
- soluble dyes e.g. Solvent Red, Solvent Yellow, Solvent Orange, Solvent Blue, Solvent Green, Solvent Violet, Solvent Brown or Solvent Black.
- Such inks can also contain other additives as listed above for aqueous inks.
- TCP 2: 1.
- the following solution of two anionic surfactants is used as the dispersant: 10 g phenylsulfonate HSR paste (65%), Hoechst AG 1 , 3 g of Nekass BX paste (62.5%), BASF AG, 13.7 water, 1.6 g of the surfactant solution are used per g of UV absorber and TCP.
- UV absorber and possibly TCP are dissolved in a little ethyl acetate.
- a solution of 3.27 g polyvinyl alcohol (PVA) in 68 g water is mixed with the surfactant solution and this mixture is mixed with the ethyl acetate solution of the UV absorber using a magnetic stirrer.
- the mixing ratios can be seen in Table 1.
- the ethyl acetate is removed in a rotary evaporator at 45 ° C., with a homogeneous dispersion of the oily phase in the PVA solution.
- 4.0 g of silica (type 244, Grace & Co) are added to each 3.27 g of PVA and the dispersion is homogenized with ultrasound for 30 seconds.
- the resulting coating composition is filtered through a sieve made of polyester fibers with a mesh size of 24 ⁇ m and the pH is adjusted to 7.0 by adding 2N sodium hydroxide solution.
- the coating mass (without UV absorber) contains 9.7% solids.
- UV absorbers A-1 mixture of approx. 57% and about 43%
- the coating compositions are applied with a wire spiral to photographic paper in a thickness of 50 ⁇ m.
- the coating obtained after drying with warm air has about 5 g / m 2 and contains 1 mmol of UV absorber per m 2 .
- the recording material thus prepared is printed with a yellow and a red ink in an inkjet printing device.
- the yellow ink is prepared from 5 parts of Acid Yellow 23, 50 parts of diethylene glycol and 45 parts of water.
- the red ink is prepared analogously using Acid Red 35.
- the inks are filtered through an ultrafilter with a pore size of 0.3 ⁇ m and filled into the ink cartridges of the "Think Jet" device (Hewlett-Packard).
- Test prints are prepared with a dot density of 75 dots per cm.
- the color density (intensity) of the stained areas is determined using a densitometer (Macbeth TR 924) using a Status A filter. Then the sample prints are irradiated in an Atlas Weatherometer with a xenon lamp with an illuminance of 81 klux behind a window glass filter. The color density is then measured again. The percentage loss of color density during exposure is shown in Table 2.
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH59987 | 1987-02-18 | ||
CH599/87 | 1987-02-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0280650A1 true EP0280650A1 (fr) | 1988-08-31 |
EP0280650B1 EP0280650B1 (fr) | 1992-04-08 |
Family
ID=4190721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88810092A Expired - Lifetime EP0280650B1 (fr) | 1987-02-18 | 1988-02-15 | Utilisation de dérivés déterminés de benztriazole comme agents de protection contre la lumière pour matériaux d'enregistrement pour impression à projection d'encre |
Country Status (6)
Country | Link |
---|---|
US (1) | US4926190A (fr) |
EP (1) | EP0280650B1 (fr) |
JP (1) | JP2759795B2 (fr) |
KR (1) | KR960008587B1 (fr) |
CA (1) | CA1328659C (fr) |
DE (1) | DE3869810D1 (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0673783A3 (fr) * | 1994-02-15 | 1997-06-11 | Xerox Corp | Feuilles d'enregistrement contenant des composés de purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotrieazole, tétrazole et pyrazine. |
EP0802063A1 (fr) * | 1996-04-16 | 1997-10-22 | Seiko Epson Corporation | Solution de réaction pour une méthode d'enregistrement par jet d'encre utilisantdeux liquides |
EP0826511A1 (fr) * | 1996-08-29 | 1998-03-04 | Oji Paper Co., Ltd. | Matériau d'enregistrement thermosensible |
EP0759364A3 (fr) * | 1995-08-21 | 1998-07-22 | Seiko Epson Corporation | Matériau d'enregistrement imprimé sur la surface arrière |
EP1398165A3 (fr) * | 2002-09-13 | 2004-04-21 | Fuji Photo Film Co., Ltd. | Feuille, méthode et encre pour l'enregistrement par jet d'encre |
WO2005032833A1 (fr) | 2003-10-03 | 2005-04-14 | Fuji Photo Film B.V. | Support d'enregistrement |
WO2010103021A1 (fr) | 2009-03-13 | 2010-09-16 | Basf Se | Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol |
WO2010115721A2 (fr) | 2009-04-02 | 2010-10-14 | Basf Se | Procédé permettant de réduire les lésions dues aux brûlures solaires chez les plantes |
WO2011161105A2 (fr) | 2010-06-24 | 2011-12-29 | Basf Se | Compositions herbicides |
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- 1988-02-15 DE DE8888810092T patent/DE3869810D1/de not_active Expired - Lifetime
- 1988-02-16 CA CA000559022A patent/CA1328659C/fr not_active Expired - Fee Related
- 1988-02-17 KR KR88001693A patent/KR960008587B1/ko not_active IP Right Cessation
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US6846525B2 (en) | 1993-03-19 | 2005-01-25 | Xerox Corporation | Recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, and pyrazine compounds |
EP0673783A3 (fr) * | 1994-02-15 | 1997-06-11 | Xerox Corp | Feuilles d'enregistrement contenant des composés de purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotrieazole, tétrazole et pyrazine. |
EP0759364A3 (fr) * | 1995-08-21 | 1998-07-22 | Seiko Epson Corporation | Matériau d'enregistrement imprimé sur la surface arrière |
EP0802063A1 (fr) * | 1996-04-16 | 1997-10-22 | Seiko Epson Corporation | Solution de réaction pour une méthode d'enregistrement par jet d'encre utilisantdeux liquides |
EP0826511A1 (fr) * | 1996-08-29 | 1998-03-04 | Oji Paper Co., Ltd. | Matériau d'enregistrement thermosensible |
US5935900A (en) * | 1996-08-29 | 1999-08-10 | Ojl Paper Co., Ltd. | Heat sensitive recording material |
US7059715B2 (en) | 2002-09-13 | 2006-06-13 | Fuji Photo Film Co., Ltd. | Sheet for ink jet recording, ink for ink jet recording, manufacturing method of ink for ink jet recording, ink set for ink jet recording, and ink jet recording method |
EP1398165A3 (fr) * | 2002-09-13 | 2004-04-21 | Fuji Photo Film Co., Ltd. | Feuille, méthode et encre pour l'enregistrement par jet d'encre |
US7399349B2 (en) | 2002-09-13 | 2008-07-15 | Fujifilm Corporation | Sheet for ink jet recording, ink for ink jet recording, manufacturing method of ink for ink jet recording, ink set for ink jet recording, and ink jet recording method |
WO2005032833A1 (fr) | 2003-10-03 | 2005-04-14 | Fuji Photo Film B.V. | Support d'enregistrement |
US8404263B2 (en) | 2008-06-20 | 2013-03-26 | Basf Se | Agrochemical formulations comprising a pesticide, an organic UV-photoprotective filter and coated metal-oxide nanoparticles |
WO2010103021A1 (fr) | 2009-03-13 | 2010-09-16 | Basf Se | Composition comprenant un pesticide et un absorbeur d'uv au benzotriazol |
WO2010115721A2 (fr) | 2009-04-02 | 2010-10-14 | Basf Se | Procédé permettant de réduire les lésions dues aux brûlures solaires chez les plantes |
US9034955B2 (en) | 2009-05-15 | 2015-05-19 | Basf Se | High molecular weight nonpolar benzotriazoles |
US9125411B2 (en) | 2010-04-15 | 2015-09-08 | Basf Se | UV absorbers for reducing the E/Z isomerization of pesticides |
WO2011161105A2 (fr) | 2010-06-24 | 2011-12-29 | Basf Se | Compositions herbicides |
WO2019192982A1 (fr) | 2018-04-04 | 2019-10-10 | Basf Se | Utilisation d'une composition polymère absorbant le rayonnement ultraviolet (uvrap) comme agent absorbant les uv dans un revêtement pour matières non vivantes et non kératiniques |
US11773277B2 (en) | 2018-04-04 | 2023-10-03 | Basf Se | Use of an ultraviolet radiation absorbing polymer composition (UVRAP) as an UV absorbing agent in a coating for non-living and non-keratinous materials |
Also Published As
Publication number | Publication date |
---|---|
KR960008587B1 (en) | 1996-06-28 |
DE3869810D1 (de) | 1992-05-14 |
JP2759795B2 (ja) | 1998-05-28 |
JPS63222885A (ja) | 1988-09-16 |
CA1328659C (fr) | 1994-04-19 |
US4926190A (en) | 1990-05-15 |
EP0280650B1 (fr) | 1992-04-08 |
KR890012980A (ko) | 1989-09-20 |
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