EP0280650B1 - 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 PDF

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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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EP
European Patent Office
Prior art keywords
formula
compound
recording material
ink
hydrogen
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.)
Expired - Lifetime
Application number
EP88810092A
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German (de)
English (en)
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EP0280650A1 (fr
Inventor
Hugh Dr. Laver
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.)
BASF Schweiz AG
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Ciba Geigy AG
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Filing date
Publication date
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Publication of EP0280650A1 publication Critical patent/EP0280650A1/fr
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Expired - Lifetime legal-status Critical Current

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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)

Claims (12)

1. Application de composés répondant à l'une des formules I et II :
Figure imgb0062
Figure imgb0063
 dans lesquelles :
n est égal à 1 ou à 2
R représente l'hydrogène, un alkyle en C₁-C₁₂, un cycloalkyle en C₅-C₈, un phényle ou un phénylalkyle en C₇-C₉,
R¹ représente l'hydrogène, le chlore ou un méthoxy,
R² représente :
a) dans le cas où n est égal à 1, un radical
Figure imgb0064
 un radical
Figure imgb0065
 ou un radical
Figure imgb0066
 dans lesquels u désigne un nombre de 1 à 9, v un nombre de 1 à 6 et w un nombre de 1 à 6,
b) dans le cas où n est égal à 2, un radical
Figure imgb0067
 ou un radical
Figure imgb0068
 dans lesquels x désigne un nombre de 1 à 7 et y un nombre de 1 à 4,
R³ représente l'hydrogène, un alkyle en C₁-C₁₈ porteur d'un ou de plusieurs -OH ou -O-COR¹⁰, un alkyle en C₃-C₃₀ interrompu par un ou plusieurs -O- ou -N(R⁷)- et éventuellement porteur d'un ou de plusieurs radicaux -OH ou -O-COR¹⁰, un cycloalkyle en C₅-C₁₂ non substitué ou porteur d'un -OH, un alcényle en C₂-C₁₈ non substitué ou porteur d'un -OH, un phénylalkyle en C₇-C₁₅, un alkylphényl-alkyle, un glycidyle, un furfuryle ou un glycosyle,
R⁷ représente l'hydrogène ou un alkyle en C₁-C₁₈,
R¹⁰ représente un alkyle en C₁-C₁₈ ou un phényle, R¹¹ représente un alcane-triyle en C₃-C₁₀ et R¹² représente un alcane-tétrayle en C₄-C₁₂,
comme stabilisants à la lumière pour des matières d'enregistrement destinées à l'impression par jet d'encre.
2. Application selon la revendication 1 de composés de formule II.
3. Application selon la revendication 1 de composés de formule I qui sont liquides à la température ambiante.
4. Matière d'enregistrement pour l'impression par jet d'encre, stabilisée contre la dégradation par la lumière, constituée d'un article planiforme bidimensionnel ayant une surface imprimable par jet d'encre, matière caractérisée en ce que la surface imprimable contient au moins un composé de formule I selon la revendication 1.
5. Matière d'enregistrement selon la revendication 4, caractérisée en ce que l'article planiforme est un papier revêtu.
6. Matière d'enregistrement selon la revendication 4, caractérisée en ce que la surface imprimable contient, en plus du composé de formule I, un accepteur cationique de colorants.
7. Matière d'enregistrement selon la revendication 4, caractérisée en ce que la surface imprimable contient, en plus du composé de formule I, un anti-oxydant, un stabilisant à la lumière supplémentaire, un azureur optique et/ou un biocide.
8. Procédé pour fabriquer une matière d'enregistrement destinée à l'impression par jet d'encre, stabilisée contre la dégradation à la lumière, procédé caractérisé en ce qu'on revêt un support bidimensionnel avec un produit de revêtement qui contient au moins un composé de formule I selon la revendication 1.
9. Procédé selon la revendication 8 caractérisé en ce que le produit de revêtement contient un liant aqueux et en ce que le composé de formule I est dispersé de façon homogène sous la forme d'une phase huileuse dans la phase aqueuse du produit de revêtement, le composé de formule I pouvant alors se trouver sous la forme d'une solution dans un liquide huileux.
10. Procédé selon la revendication 8 caractérisé en ce qu'on ajoute un surfactif à la phase aqueuse ou à la phase huileuse.
11. Composé répondant à la formule II :
Figure imgb0069
 dans laquelle R et R³ ont les significations qui leur ont été données à la revendication 1.
12. Composés de formule II selon la revendication 11 dans lesquels R représente un radical tert-butyle.
EP88810092A 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 Expired - Lifetime EP0280650B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH599/87 1987-02-18
CH59987 1987-02-18

Publications (2)

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EP0280650A1 EP0280650A1 (fr) 1988-08-31
EP0280650B1 true EP0280650B1 (fr) 1992-04-08

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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)

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US7878644B2 (en) 2005-11-16 2011-02-01 Gerber Scientific International, Inc. Light cure of cationic ink on acidic substrates

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US9125411B2 (en) 2010-04-15 2015-09-08 Basf Se UV absorbers for reducing the E/Z isomerization of pesticides
JP2013529615A (ja) 2010-06-24 2013-07-22 ビーエーエスエフ ソシエタス・ヨーロピア 除草剤組成物
EP3068839B1 (fr) 2013-10-29 2019-01-16 Basf Se Utilisation de composés de 2-(2-hydroxyphényl) benzotriazole comme agent absorbant des uv dans des revêtements
CN110799502B (zh) * 2017-07-07 2022-12-30 奇钛科技股份有限公司 反应型紫外光吸收剂及其应用
JP7337835B2 (ja) 2018-04-04 2023-09-04 ビーエーエスエフ ソシエタス・ヨーロピア 非生物および非ケラチン性物質のコーティングにおけるｕｖ吸収剤としての紫外線吸収性ポリマー組成物（ｕｖｒａｐ）の使用
EP3653393A1 (fr) * 2018-11-19 2020-05-20 Kaspar Papir Pte Ltd Support de transfert à stabilisation légère
WO2020104307A1 (fr) * 2018-11-19 2020-05-28 Kaspar Papir Pte Ltd Support de transfert stabilisant la lumiere
CN109912771B (zh) * 2019-03-20 2021-10-12 浙江华峰热塑性聚氨酯有限公司 低析出长效耐黄变热塑性聚氨酯弹性体及其制备方法

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EP0759364A2 (fr) * 1995-08-21 1997-02-26 Seiko Epson Corporation Matériau d'enregistrement imprimé sur la surface arrière
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

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DE3869810D1 (de) 1992-05-14
US4926190A (en) 1990-05-15
JP2759795B2 (ja) 1998-05-28
CA1328659C (fr) 1994-04-19
KR890012980A (ko) 1989-09-20
JPS63222885A (ja) 1988-09-16
KR960008587B1 (en) 1996-06-28
EP0280650A1 (fr) 1988-08-31

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