EP0280650B1 - Verwendung von bestimmten Benztriazolderivaten als Lichtschutzmittel für Aufzeichnungsmaterialien für den Tintenstrahldruck - Google Patents
Verwendung von bestimmten Benztriazolderivaten als Lichtschutzmittel für Aufzeichnungsmaterialien für den Tintenstrahldruck Download PDFInfo
- Publication number
- EP0280650B1 EP0280650B1 EP88810092A EP88810092A EP0280650B1 EP 0280650 B1 EP0280650 B1 EP 0280650B1 EP 88810092 A EP88810092 A EP 88810092A EP 88810092 A EP88810092 A EP 88810092A EP 0280650 B1 EP0280650 B1 EP 0280650B1
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- European Patent Office
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- compound
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- hydrogen
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- 239000000463 material Substances 0.000 title claims description 37
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 4
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- 150000001875 compounds Chemical class 0.000 claims description 27
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- 238000007641 inkjet printing Methods 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- 125000003147 glycosyl group Chemical group 0.000 claims description 2
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- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 150000002009 diols Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 239000006174 pH buffer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- MTGYZMXZHZOFCT-UHFFFAOYSA-N pentadecoxybenzene Chemical compound CCCCCCCCCCCCCCCOC1=CC=CC=C1 MTGYZMXZHZOFCT-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- YMAHRBGBVUOIMQ-UHFFFAOYSA-N pentyl 2-methylbenzoate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C YMAHRBGBVUOIMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical group CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical group CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- ZOPCDOGRWDSSDQ-UHFFFAOYSA-N trinonyl phosphate Chemical group CCCCCCCCCOP(=O)(OCCCCCCCCC)OCCCCCCCCC ZOPCDOGRWDSSDQ-UHFFFAOYSA-N 0.000 description 1
- BGNTUSKZDOUZCZ-UHFFFAOYSA-N tris(1-butoxyethyl) phosphate Chemical compound CCCCOC(C)OP(=O)(OC(C)OCCCC)OC(C)OCCCC BGNTUSKZDOUZCZ-UHFFFAOYSA-N 0.000 description 1
- SVETUDAIEHYIKZ-IUPFWZBJSA-N tris[(z)-octadec-9-enyl] phosphate Chemical group CCCCCCCC\C=C/CCCCCCCCOP(=O)(OCCCCCCCC\C=C/CCCCCCCC)OCCCCCCCC\C=C/CCCCCCCC SVETUDAIEHYIKZ-IUPFWZBJSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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 inkjet printing and to the recording materials stabilized by means of these compounds against damage to light.
- R3 can also be OH substituted cycloalkyl, e.g. 4-hydroxycyclohexyl.
- R3 as C7-C15 phenylalkyl or alkylphenylalkyl can e.g. Benzyl, 2-phenylethyl, 1-phenylethyl, 3-phenylpropyl, 2-phenylpropyl-2, 4-methylbenzyl or 4-octylbenzyl.
- Examples of this are the compounds 8), 20), 23), 28), 34), 47) and 51) listed above or mixtures of 3) and 24), of 19) and 29), of 33) and 46) or of 5), 26), 33) and 46).
- New compounds and as such also the subject of the invention are the compounds of formula IIV, where R and R3 have the meanings given above.
- 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 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.
- 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 used to prepare the dispersions which is removed again during the production process of the recording material.
- low volatility solvents are organic liquids of an oily character and with a high boiling point, such as phthalic acid esters (eg dimethyl, diethyl, dibutyl, diamyl, dihexyl, diheptyl, dioctyl, dinonyl or didecyl phthalate, or dibutyl chlorophthalate) , Glycolic acid esters (e.g.
- O-acetyl-triethyl) O-acetyl-triethyl
- tributyl trihexyl, trioctyl, trinonyl or tridecyl citrate
- benzoic acid esters e.g. butyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl , Octadecyl or oleyl benzoate
- esters of substituted benzoic acids e.g.
- 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.
- 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.
- Examples of 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 betaine, N-alkyl- ⁇ -aminopropionic acids or alkylene bis (amidoalkylglycinates).
- the following surfactants have proven particularly useful as dispersing agents for the oily phase which contains the UV absorber:
- alkylarylsulfonates can be increased by adding wetting agents, which are also surfactants.
- wetting agents include sodium dioctyl sulfosuccinate and alkyl naphthalenesulfonates.
- 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.
- TCP 2: 1.
- the following solution of two anionic surfactants is used as the dispersant: 10 g phenyl sulfonate HSR paste (65%), Hoechst AG 1.3 g Nekal® BX paste (62.5%), BASF AG, 13.7g water.
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 |
|---|---|---|---|
| CH599/87 | 1987-02-18 | ||
| CH59987 | 1987-02-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0280650A1 EP0280650A1 (de) | 1988-08-31 |
| EP0280650B1 true EP0280650B1 (de) | 1992-04-08 |
Family
ID=4190721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88810092A Expired - Lifetime EP0280650B1 (de) | 1987-02-18 | 1988-02-15 | Verwendung von bestimmten Benztriazolderivaten als Lichtschutzmittel für Aufzeichnungsmaterialien für den Tintenstrahldruck |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4926190A (ko) |
| EP (1) | EP0280650B1 (ko) |
| JP (1) | JP2759795B2 (ko) |
| KR (1) | KR960008587B1 (ko) |
| CA (1) | CA1328659C (ko) |
| DE (1) | DE3869810D1 (ko) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0673783A2 (en) * | 1994-02-15 | 1995-09-27 | Xerox Corporation | Recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, and pyrazine compounds |
| EP0759364A2 (en) * | 1995-08-21 | 1997-02-26 | Seiko Epson Corporation | Back print recording medium |
| US7878644B2 (en) | 2005-11-16 | 2011-02-01 | Gerber Scientific International, Inc. | Light cure of cationic ink on acidic substrates |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0373573B1 (de) * | 1988-12-14 | 1994-06-22 | Ciba-Geigy Ag | Aufzeichnungsmaterial für Tintenstrahldruck |
| US5096781A (en) * | 1988-12-19 | 1992-03-17 | Ciba-Geigy Corporation | Water-soluble compounds as light stabilizers |
| GB2230784B (en) * | 1989-03-21 | 1992-11-18 | Ciba Geigy Ag | Process for modifying acrylate copolymers |
| EP0415880B1 (de) * | 1989-08-25 | 1995-04-05 | Ciba-Geigy Ag | Lichtstabilisierte Tinten |
| DE4116595A1 (de) * | 1991-05-22 | 1992-11-26 | Schoeller Felix Jun Papier | Aufzeichnungsmaterial fuer das tintenstrahlaufzeichnungsverfahren |
| US5441795A (en) * | 1993-03-19 | 1995-08-15 | Xerox Corporation | Recording sheets containing pyridinium compounds |
| US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
| US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
| US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
| US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
| US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
| US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
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| US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
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| US4256493A (en) * | 1979-10-04 | 1981-03-17 | Dai Nippon Tokyo Co., Ltd. | Jet ink composition |
| JPS5787988A (en) * | 1980-11-21 | 1982-06-01 | Matsushita Electric Ind Co Ltd | Ink jet recording paper |
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| US4853471A (en) * | 1981-01-23 | 1989-08-01 | Ciba-Geigy Corporation | 2-(2-Hydroxyphenyl)-benztriazoles, their use as UV-absorbers and their preparation |
| EP0133164B1 (de) * | 1983-07-26 | 1988-12-14 | Ciba-Geigy Ag | Copolymerisierbare Verbindungen |
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| US4547405A (en) * | 1984-12-13 | 1985-10-15 | Polaroid Corporation | Ink jet transparency |
-
1988
- 1988-02-08 US US07/153,695 patent/US4926190A/en not_active Expired - Lifetime
- 1988-02-15 EP EP88810092A patent/EP0280650B1/de not_active Expired - Lifetime
- 1988-02-15 DE DE8888810092T patent/DE3869810D1/de not_active Expired - Lifetime
- 1988-02-16 CA CA000559022A patent/CA1328659C/en not_active Expired - Fee Related
- 1988-02-17 KR KR88001693A patent/KR960008587B1/ko not_active IP Right Cessation
- 1988-02-18 JP JP63036461A patent/JP2759795B2/ja not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0673783A2 (en) * | 1994-02-15 | 1995-09-27 | Xerox Corporation | Recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, and pyrazine compounds |
| EP0759364A2 (en) * | 1995-08-21 | 1997-02-26 | Seiko Epson Corporation | Back print recording medium |
| US7878644B2 (en) | 2005-11-16 | 2011-02-01 | Gerber Scientific International, Inc. | Light cure of cationic ink on acidic substrates |
| US7896485B2 (en) | 2005-11-16 | 2011-03-01 | Gerber Scientific International, Inc. | Light cure of cationic ink on acidic substrates |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3869810D1 (de) | 1992-05-14 |
| EP0280650A1 (de) | 1988-08-31 |
| CA1328659C (en) | 1994-04-19 |
| US4926190A (en) | 1990-05-15 |
| KR890012980A (ko) | 1989-09-20 |
| JP2759795B2 (ja) | 1998-05-28 |
| JPS63222885A (ja) | 1988-09-16 |
| KR960008587B1 (en) | 1996-06-28 |
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