Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/091—Azo dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/0912—Indigoid; Diaryl and Triaryl methane; Oxyketone dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/0918—Phthalocyanine dyes

Definitions

• the present invention relates to a coloured toner suitable for use in electrophotographic applications such as electroreprography and laser printing containing a solvent-soluble metal phthalocyanine blue dyestuff and to a trichomatic set of toners comprising said toner together with a coloured toner containing a red benzodifuranone dyestuff and a coloured toner containing an yellow azo pyridone dyestuff.
• pigments in coloured toners such as those found in colour photocopiers. Pigments generally have good heat and light fastness together with low bleed characteristics in the substrate to which they are applied. However, pigments are generally tinctorially weak, difficult to use and the limited number of pigments available restricts the shade gamut. Furthermore, pigments generally exhibit poor diffusion properties in substrates and tend to be opaque which is particularly restrictive in the case of substrates used as overhead transparencies.
• US patent no.4 395 471 dicloses a developer composition which comprises a resin, one or more cyan, magenta and yellow colorants and a single carrier and differs from the present invention in the selection of the red and yellow colorants.
• a trichomatic set of coloured toners comprising a blue toner containing a phthalocyanine dyestuff of formula I together with a red toner containing a benzodifuranone dyestuff and a yellow toner containing an azo pyridone dyestuff.
• the dyestuffs used in these toners are hereinafter referred to as Pc, BDF and AP dyestuffs respectively.
• the metal containing phthalocyanine is of formula I M Pc --(-SO 2 NHR) y I wherein
• the alkyl group may be linear or branched and preferably contains at least 8 carbon atoms, more preferably at least 12 carbon atoms and especially at least 16 carbon atoms, for example 18 carbon atoms.
• M is preferably copper.
• the BDF dyestuff is of formula II wherein
• R 1 to R 8 When R 1 to R 8 is, or contains, alkyl, alkenyl or alkylene it may be linear or branched, but is especially linear.
• the substituents in the rings A and B are different, the difference lying in either the identity of the groups R 1 to R 4 and -OR 5 carried by the two rings at the position of attachment of such groups to the rings.
• the dyestuff of formula II is asymmetrical.
• R 1 and R 2 are both H, C 1-4 -alkyl or C 1-4 -alkoxy or that R 1 is C 1-4 -alkyl or C 1-4 -alkoxy and R 2 is H and it is also preferred that R 1 is in the para position.
• R 3 and R 4 are both H, C 1-4 -alkyl or C 1-4 -alkoxy or that R 3 is C 1-4 -alkyl or C 1-4 -alkoxy and R 4 is H and it is further preferred that R 3 is in the ortho position to the group -OR 5 .
• R 1 is in the para position of ring A and that R 3 and R 4 are both H.
• R 5 is alkyl, it is preferably C 1-4 -alkyl.
• the alkyl groups forming the whole or part of R 6 , R 7 and R 8 are preferably C 1-4 -alkyl.
• q is 1, and Z is -OR 6 , and in another preferred group q is O, (C 1-3 -alkylene) is -CH 2 -CH 2 - or -CH 2 CH 2 CH 2 - or -CH 2 CH(CH 3 )- and Z is - OR 8 .
• (C 1-3 -alkylene) is -CH 2 - or -CH 2 CH 2 - and especially -CH 2 -.
• Z is -OR 6 and that R 6 is preferably C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl or a second group represented by R 5 .
• R 6 is a second group represented by R 5
• alkylene is linear
• p is 1
• Z is C 1-4 -alkoxy or C 1-4 -alkoxy-C 1-4 -alkyl.
• Z is -NR 6 R 7 , it is preferred that both R 6 and R 7 are C 1-4 -alkyl.
• q is O and (C 1-3 -alkylene) is preferably -CH 2 CH 2 -. It is also preferred that Z is -OR 8 and that R 8 is C 1-4 -alkyl or C 1-4 -alkoxy-C 1-4 -alkyl.
• R 5 may be a group of formula -(C 1-3 -alkylene)-CO-Z wherein
• (C 1-3 -alkylene) is -CH 2 - or -CH 2 CH 2 - and especially -CH 2 -.
• Z is -OR 6 in which R 6 is preferably C 1-4 -alkyl, C 1-4 -alkoxy-C 1-4 -alkyl or a group represented by R 5 in which p is 1 and R 6 is C 1-4 -alkyl or C 1-4 -alkoxy-C 1-4 -alkyl.
• substituents in ring A are 4-methyl, 4-methoxy and 4-propoxy.
• the BDF dyestuff is selected from 3-[4-n-propoxyphenyl]-7-[4(2-ethoxyethoxycarbonylmethoxy)-phenyl]-2,6-dioxo-2,6-dihydrobenzo[1:2-b, 4:5-b 1 ]difuran (Red 1), 3-phenyl-7-[4-n-propoxyphenyl]-2,6-dioxo-2,6-dihydrobenzo-[1:2-b,4:5-b 1 ]difuran (Red 2) and 3-phenyl-7-[4-(2-ethoxyethoxy-carbonylmethoxy)-phenyll-2,6-dioxo-2,6-dihydrobenzo[1:2-b,4:5-b 1 ]-difuran (Red 3).
• the AP dyestuff is of formula III wherein
• the alkyl group may be linear or branched.
• X is halogen, it is preferably iodine, bromine and especially chlorine.
• R 5 is C 1-4 -alkyl-C 1-4 -alkoxy or C 1-4 -alkyl-C 1-4 -alkoxy-C 1-4 -alkoxy.
• R 9 is methyl
• n is preferably 1 or 2.
• the group X is preferably in the 2 and/or 4 position of the phenyl ring relative to the azo group.
• Examples of the group X include 2-nitro, 4-chloro and 2-chloro-4-nitro.
• R 10 examples include methyl, ethyl, butyl and 2-ethylhexyl.
• Examples of the group -COOR 5 include methoxyethoxycarbonyl and methoxyethoxyethoxycarbonyl.
• the dyestuffs of formula III may be prepared by any means known to the art and are generally made by diazotising an amine and coupling with a pyridone coupler.
• An especially preferred trichomatic set of coloured toners comprises three toners containing Yellow 1, Red 3 and CI Solvent Blue 70 respectively.
• Each toner in the trichomatic toner set preferably comprises a toner resin, a dye and a charge control agent (hereafter CCA).
• the CCA is preferably colourless and may be cationic or anionic
• a preferred cationic CCA is a quaternary ammonium compound such as cetyl pyridinium chloride or bromide as positively charged CCA.
• a preferred anionic CCA is a metal complex or salt, for example a 2:1 metal complex or salt of a hydroxynaphthoic acid as a negatively charged CCA.
• a preferred anionic CCA is BONTRON E81 (BONTRON is a registered trade mark of Orient, Japan).
• the toner resin is preferably a thermoplastic resin suitable for use in the preparation of toner resins.
• Suitable toner resins include a styrene or substituted styrene polymer or copolymer such as polystyrene or styrene-butadiene copolymer, a styrene-acrylic copolymer, such as a styrene-butyl methacrylate copolymer, alkoxylated bis-phenol based polymers such as those described in US 5,143,809; polyvinyl acetate; polyalkenes; poly(vinyl chloride); polyurethanes; polyamides; silicones; epoxy resins and phenolic resins.
• the toner resin is a polyester since the dyestuffs used in the toner trichomatic set of the present invention are more compatible with and hence easier to formulate in such resins and produce clear, durable and bright reprographic images, especially on overhead transparencies.
• the resin has a melting point between 120 and 220°C and more preferably between 140 and 180°C.
• the amount of dyestuff in each toner is preferably from 0.1 to 10% by weight of the toner.
• the amount of dyestuff is more preferably at least 0.5% and especially at least 1% and more preferably up to 7% and especially up to 5% by weight of the toner.
• the amount of CCA in the toner is preferably at least 0.1%, more preferably at least 0.5% and especially at least 1% by weight of the toner.
• the amount of CCA is desirably up to 12%, preferably up to 10% more preferably up to 5% and especially up to 3% by weight of the toner.
• the toner may be prepared by any method known to the art and typically involves mixing a toner resin with a CCA and a dyestuff by kneading in a ball mill above the melting point of the resin in order to uniformly distribute the CCA and dye throughout the resin. The toner is then cooled, crushed and micronised until the mean diameter of the particles is less than 100 ⁇ , preferably less than 50 ⁇ , more preferably less than 20%, and especially less than 10 ⁇ ,. The powdered toner so obtained may be used directly or may be diluted with an inert solid diluent such as fine silica.
• the dye and CCA may be added simultaneously or sequentially to the resin before or after melting the resin, but are preferably added to the resin when molten.
• the coloured toner containing a metal Pc dyestuff and the trichomatic set of toners comprising the toner containing a metal Pc dyestuff, a toner containing a BDF dyestuff and a toner containing an AP dyestuff can be used in an analogous manner to conventional colour toners containing pigments as described, for example, in US 5,102,764; US 5,032,483 and EP 159,166.
• the toner containing the metal Pc dyestuff is a copper Pc dyestuff since this provides for a wide gamut of shades when used in conjunction with a toner containing a BDF dyestuff and a toner containing an AP dyestuff.
• the gamut of shades obtained using this trichomatic set of toners can be usefully extended when the set further comprises a toner containing a nickel Pc dyestuff.
• a trichomatic set of toners which further comprises a toner containing a nickel Pc dyestuff of Formula 1.
• the blue toner and the trichomatic set of coloured toners are of use in colour electrophotography for producing colour images on sheet or film material, especially paper and transparencies, particularly transparencies made from plastics materials, especially polyester and acetate plastics material. They have been found particularly useful for overhead transparencies because of the brightness and intensity of the colours and the fastness properties of the images, and are especially useful for laser printing of paper.
• Polyester resin 300 parts; ALMACRYL XPE 1299, ZENECA Resins
• CI Solvent Blue 70 2 parts was added over 5 minutes with blending followed by BONTRON E81(3 parts) added over 5 minutes. After mixing for a further 30 minutes the resultant blue coloured resin was cooled, ground and micronised until the mean particle size was between 3 ⁇ and 10 ⁇ .
• Example 1 The copper phthalocyanine dyestuff used in Example 1 was replaced with the equivalent amount of the nickel analogue.
• the toner so obtained produced clear bluish-green prints on overhead polyester transparencies with similar excellent fastness properties.

Applications Claiming Priority (3)

Publications (2)

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ID=10737899

Family Applications (1)

Country Status (8)

Cited By (2)

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• 1993
  • 1993-06-28 GB GB939313274A patent/GB9313274D0/en active Pending
• 1994
  • 1994-03-29 JP JP7502537A patent/JPH08511879A/ja active Pending
  • 1994-03-29 DE DE69405750T patent/DE69405750T2/de not_active Expired - Fee Related
  • 1994-03-29 CA CA002161891A patent/CA2161891A1/en not_active Abandoned
  • 1994-03-29 EP EP94912006A patent/EP0706679B1/en not_active Expired - Lifetime
  • 1994-03-29 WO PCT/GB1994/000655 patent/WO1995000885A1/en active IP Right Grant
  • 1994-03-29 KR KR1019950705752A patent/KR960703246A/ko not_active Application Discontinuation
• 1998
  • 1998-03-11 HK HK98102027A patent/HK1002940A1/xx not_active IP Right Cessation

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