WO1996034916A2 - Composition d'encre - Google Patents

Composition d'encre Download PDF

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Publication number
WO1996034916A2
WO1996034916A2 PCT/GB1996/000994 GB9600994W WO9634916A2 WO 1996034916 A2 WO1996034916 A2 WO 1996034916A2 GB 9600994 W GB9600994 W GB 9600994W WO 9634916 A2 WO9634916 A2 WO 9634916A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
water
preparation
independently
Prior art date
Application number
PCT/GB1996/000994
Other languages
English (en)
Other versions
WO1996034916A3 (fr
Inventor
Roy Bradbury
Alan Butters
Clive Moscrop
Andrew Slark
Original Assignee
Zeneca Limited
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
Priority claimed from GBGB9508810.0A external-priority patent/GB9508810D0/en
Priority claimed from GBGB9508874.6A external-priority patent/GB9508874D0/en
Application filed by Zeneca Limited filed Critical Zeneca Limited
Priority to EP96911052A priority Critical patent/EP0823927A2/fr
Priority to JP8533099A priority patent/JPH11504958A/ja
Priority to US08/945,649 priority patent/US6099625A/en
Publication of WO1996034916A2 publication Critical patent/WO1996034916A2/fr
Publication of WO1996034916A3 publication Critical patent/WO1996034916A3/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • D06P5/004—Transfer printing using subliming dyes
    • D06P5/006—Transfer printing using subliming dyes using specified dyes
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • 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
    • B41M5/5245—Macromolecular coatings characterised by the use of polymers containing cationic or anionic groups, e.g. mordants
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3852—Anthraquinone or naphthoquinone dyes
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3854—Dyes containing one or more acyclic carbon-to-carbon double bonds, e.g., di- or tri-cyanovinyl, methine
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3856—Dyes characterised by an acyclic -X=C group, where X can represent both nitrogen and a substituted carbon atom
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/388—Azo dyes
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine

Definitions

  • the present invention relates to compounds, compositions and solutions thereof, suitable for use in printing and imaging technologies, especially those suitable for coloration of substrates such as paper, plastics, textiles, metal and glass by printing processes such as inkjet printing and those suitable for use in electrophotography such as charge control agents (CCA), charge transfer materials (CTM), charge generating materials (CGM) and toners.
  • CCA charge control agents
  • CTM charge transfer materials
  • CGM charge generating materials
  • Inkjet printing is a non-impact printing technique which involves ejecting, thermally or by action of an oscillating piezo crystal, droplets of ink continuously or on demand from a fine nozzle directly onto a substrate such as paper, plastics, textile, metal or glass.
  • the ink may be aqueous, solvent or hot melt based and must provide sharp, non-feathered images which have good waterfastness, light fastness and optical density, have fast fixation to the substrate and cause no clogging of the nozzle.
  • Electrophotographic copiers or printers generally comprise an organic photoconductor (OPC) and a developer or toner.
  • OPC organic photoconductor
  • the OPC generally comprises an electrically conducting support, a charge generating layer and a charge transport layer.
  • the electrically conducting support is a metal drum, typically an aluminium drum, or a metallised polymer film, typically aluminised polyester.
  • the charge generating layer comprises a charge generating material (CGM) and a binder resin, typically a polycarbonate.
  • the charge transport later comprises a charge transport material (CTM) and a binder resin, typically a polycarbonate.
  • the developer or toner comprises a toner resin, a colorant and optionally a charge control agent (CCA).
  • the toner resin is typically a styrene or substituted styrene polymer or styrene-butadiene copolymer.
  • the colorant is typically a dye or pigment or mixture thereof.
  • an ink composition comprising a compound of Formula (1 ) and salts thereof:
  • Ch represents an arrangement of atoms which causes the compound to absorb electromagnetic radiation;
  • R a and R each independently is a spacer group;
  • Y is an interactive functional group; w and x each independently is 0 or an integer equal to or greater than 1 ; and m and n each independently is an integer equal to or greater than 1 , provided that w and x are not both equal to zero and when one of w or x is 0 at least one of m and n is equal to or greater than 2.
  • the compound may absorb radiation in the UV, visible or infra-red region of the electromagnetic spectrum.
  • the chromogen represented by Ch is preferably an optionally substituted group of Formula (2):
  • R 1 and R 2 each independently is -H, or optionally substituted alkyl or alkoxy or an optionally substituted group of Formula (2B):
  • T is A 1 -NH or optionally substituted phenyl (such as optionally substituted mono- or dialkylaminophenyl), T 1 is optionally substituted C ⁇ -12-alkyl or optionally substituted aryl, and T 2 is optionally substituted alkyl; or an optionally substituted group of Formula (3):
  • R c and R d each independently is H, alkyl, alkoxy or halogen and Ring A and Ring B may carry from 1 to 5 optional substituents; or an optionally substituted group of Formula (5):
  • X is -C(R) or N and R is H, CN or COOalkyl; and A is A 1 -N in which A 1 is the residue of a diazotisable aromatic or heteroaromatic amine or is selected from an optionally substituted group of Formula (6):
  • X 1 , Y and Z each independently is N or C-R 3 in which R 3 is -H, -CN alkyl, alkoxy, cycloalkyl, aryl, aralkyl, aryloxy or amino; or an optionally substituted group of Formula (8):
  • R 4 and R 5 are as hereinbefore defined; or an optionally substituted group of Formula (10):
  • R 3 is as hereinbefore defined and R 6 is alkenyl or
  • R z is NH 2 , phenyl or succinamido; or an optionally substituted group of Formula (11):
  • R 4 and R 5 each independently is preferably -CN, -NO 2 , -COOH or -COOC ⁇ -alkyl.
  • a 1 is preferably selected from phenyl, naphthyl, thiazolyl, isothiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, thiadiazolyl, imidazolyl, thienyl, pyridyl and pyridoisothiazolyl each of which may be optionally substituted.
  • a 1 is phenyl it is preferably of the Formula (12):
  • R 8 is -H, optionally substituted alkyl, optionally substituted alkoxy, -NO 2 , -CN, -CF 3 , -SCN, halogen, alkoxyalkyl, -COalkyl, -OCOalkyl, -COOalkyl, -SO 2 NH 2 , -SO 2 F, -SO 2 CI,
  • a 1 is naphthyl it is preferably a naphth-1-yl of the Formula (13):
  • R 8 is as hereinbefore defined; and n 2 is an integer from 1 to 4.
  • a 1 is thiazolyl it is preferably a thiazol-2-yl of the Formula (14):
  • R 9 is -H or optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, halogen or -Salkyl; and R 10 is -H, optionally substituted alkyl, alkenyl, -CN, -NO 2 ,
  • a 1 is isothiazolyl it is preferably an isothiazol-5-yl of the Formula (15):
  • R 11 is -H, optionally substituted alkyl, optionally substituted aryl, -SO 2 alkyl,
  • R 12 is -H, -CN, -NO 2 , -SCN or -COOalkyl.
  • a 1 is benzothiazolyl it is preferably a benzothiazol-2-yl of the Formula (16):
  • R 13 is -H, -SCN, -NO 2 , -CN, halogen, optionally substituted alkyl, optionally substituted alkoxy, -COOalkyl, -OCOalkyl or -SO 2 alkyl; and n 3 is from 1 to 4.
  • a 1 is benzoisothiazolyl it is preferably a benzoisothiazol-3-yl of the Formula
  • a 1 is pyrazolyl it is preferably a pyrazol-5-yl of the Formula (18):
  • each R 10 is independently as hereinbefore defined; and 14 R" is -H, optionally substituted alkyl or optionally substituted aryl.
  • a 1 is thiadiazolyl it is preferably a 1 ,2,4-thiadiazol-5-yl of Formula (19):
  • R 15 is -Salkyl, -Saryl, -SO 2 alkyl or halogen or is a 1 ,3,4-thiadiazol-5-yl of Formula (20):
  • R 15 is as hereinbefore defined.
  • a 1 is imidazolyl it is preferably an imidazol-2-yl of the Formula (21 ):
  • R 17 is -CN or -Cl
  • R 18 is -H or optionally substituted alkyl.
  • a 1 is thienyl it is preferably a thien-2-yl of the Formula (22):
  • R 19 is -NO 2 , -CN, alkylcarbonylamino or alkoxycarbonyl;
  • ROT is -H, halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl or -Salkyl;
  • R 21 is -H, optionally substituted alkyl, -CN, -NO 2 , -SO 2 alkyl,
  • a 1 is pyridyl it is preferably a pyrid-2-yl, pyrid-3-yl or pyrid-4-yl of the Formula (23):
  • R 8 is as hereinbefore defined; and n 5 is from 1 to 4.
  • a 1 is pyridoisothiazolyl it is preferably a pyridoisothiazol-3-yl of the Formula
  • R 22 is -CN or -NO 2 ; and R 23 is optionally substituted alkyl.
  • the spacer group provides some degree of insulation and limits the impact of the interactive functional group on the absorption characteristics of Ch.
  • the spacer group is an atom or group of atoms which links the spacer group to Ch by at least one ⁇ (sigma) bond and links the spacer group to Y by at least one ⁇ (sigma) bond.
  • the spacer group preferably comprises at least one atom selected from C, Si and S more preferably C or Si and especially C. Where the spacer group is S it is preferably a divalent sulphide.
  • At least one of the spacer groups represented by R a and R b preferably comprises at least one and more preferably at least two carbon atoms.
  • R a and R b comprises two or more, more preferably three or more carbon atoms. It is further preferred that both R a and R b comprise two or more, more preferably three or more carbon atoms. It is especially preferred that R a and R b independently is C 2 - ⁇ o-alkylene and more especially C 3 . 10 -alkylene.
  • a preferred subgroup of compounds of Formulae (1) to (5) is that in which R a and R b each independently is C 2 . 5 -alkylene especially compounds in which R a and R b is C 2 . 5 -alkylene substituted only by a Y group.
  • the interactive functional group represented by Y are such that the Y groups on different molecules may interact with each other to form complexes of larger size and thus of lower mobility and/or the Y groups may interact the substrate.
  • the Y groups may be the same or different and the R a and R b may cany one or more Y groups.
  • the interactions between different Y groups or between the Y groups and the substrate produces a print or an image on the substrate which is resistant to water and light and which fixes rapidly.
  • the Y groups are preferably selected from OH, NH 2 , NHR 24 , COOH, CONH 2 , CONHR 24 , SO 2 NH 2 , SO 2 NHR 24 , NHCONH 2 .
  • a preferred subgroup of compound is that in which Ch is a group of Formula (2).
  • a further preferred subgroup of compounds is that in which Ch contains a substituted group comprising an ⁇ -branched N-alkyl group.
  • Ch is a group of Formula (2) and contains a substituted group comprising an ⁇ -branched N-alkyl group.
  • the present compounds have a molecular weight in the range 150 to 600.
  • the optional substituents are preferably selected from -CN, -NO 2 , -Cl, -F, -Br, C ⁇ -alkyl, d-e-alkoxy, -NHCOd-.- alkyl, NHCOphenyl, -NHSO 2 phenyl and phenoxy.
  • Particularly preferred compounds of Formula (1) are those in which Ch is an optionally substituted group of Formula (2) or Formula (2b) or Formula (3) or Formula (4) or Formula (5).
  • Especially preferred compounds of Formula (1) are those in which Ch is a optionally substituted group of Formula (2) in which X is -C(R) and A and R are as hereinbefore defined.
  • a preferred group of compounds are those in which at least one of R a and R b is C 2 . 10 -alkylene, more preferably those in which both R a and R b are C 2 - ⁇ 0 -alkylene.
  • compounds of Formula (5) it is preferred that one of R a and R is C 2 .
  • R a and R b contain S or Si or more than two C atoms in an alkylene chain
  • the compounds of the invention may be prepared by conventional methods such as those described in EP285665, EP400706, EP483791.
  • the substrate used in the inkjet printing process may be paper, plastics, textile, metal or glass and is preferably paper, plastic or a textile material, especially a natural, semi-synthetic or synthetic material.
  • natural textile materials include wool, silk, hair and cellulosic materials, particularly cotton, jute, hemp, flax and linen.
  • Examples of synthetic and semi-synthetic materials include poiyamides, polyesters, polyacrylonitriles and polyurethanes.
  • the medium for the present ink compositions may be a liquid or a low melting point solid.
  • Liquid media may be aqueous or solvent-based.
  • Aqueous-based ink compositions are generally used in office or home printers whereas solvent based ink compositions find use in industrial continuous printers.
  • the compound of Formula (1) is dissolved completely in the aqueous or solvent medium to form a solution.
  • the ink compositions of the present invention preferably contain from 0.5% to 20%, more preferably from 0.5% to 15%, and especially from 1% to 3%, by weight of the • compound of Formula (1) based on the total weight of the ink. Although many ink compositions contain less than 5% by weight of colorant, it is desirable that the compound has a solubility of around 10% or more to allow the preparation of concentrates which may be used to prepare more dilute inks and to minimise the chance of precipitation of the compound if evaporation of the liquid medium occurs during use of the ink.
  • liquid medium is aqueous based it is preferably water or a mixture of water and one or more water-soluble organic solvent.
  • the weight ratio of water to organic solvent(s) is preferably from 99:1 to 1:99, more preferably from 99:1 to 50:50 and especially from 95:5 to 80:20.
  • the water-soluble organic solvent(s) is preferably selected from d- 4 -alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol or isobutanol; amides such as dimethylformamide or dimethylacetamide; ketones or ketone-alcohols such as acetone or diacetone alcohol; ethers such as tetrahydrofuran or dioxane; oligo- or poly-alkyleneglycols such as diethylene glycol, triethylene glycol, polyethylene glycol or polypropylene glycol; alkyleneglycols or thioglycols containing a C 2 -C 6 -alkylene group such as ethylene glycol, propylene glycol, butylene glycol, pentylene glycol or hexylene glycol and thiodiglycol; polyols such as
  • Preferred water-soluble organic solvents are 2-pyrrolidone; N-methyl-pyrrolidone; alkylene- and oligo-alkylene-glycols, such as ethyleneglycol, diethyleneglycol, triethyleneglycol; and lower alkyl ethers of polyhydric alcohols such as or 2-methoxy- 2-ethoxy-2-ethoxyethanol; and polyethyleneglycols with a molecular weight of up to 500.
  • a preferred specific solvent mixture is a binary or ternary mixture of water and diethylene glycol and/or, 2-pyrrolidone or N-methylpyrrolidone in weight ratios 75-95:25-5 and 60-80:0- 20:0-20 respectively.
  • Suitable ink media are given in US 4,963,189, US 4,703,113, US 4,626,284 and EP 4,251 ,50A. According to a further aspect of the present invention there is provided a process for printing a substrate with an ink composition using an ink jet printer, characterised in that the ink composition comprises at least one compound of Formula (1).
  • a suitable process for the application of an ink composition as hereinbefore described comprises forming the ink into small droplets by ejection from a reservoir through a small orifice so that the droplets of ink are directed at a substrate.
  • This process is commonly referred to as ink jet printing, and preferred ink jet printing processes for the present inks are piezoelectric ink jet printing and thermal ink jet printing.
  • thermal ink jet printing programmed pulses of heat are applied to the ink in the reservoir by means of a resistor adjacent to the orifice, during relative movement between the substrate and the reservoir.
  • Preferred substrates include overhead projector slides or papers, including plain and treated papers, which may have an acid, alkaline or neutral character or textile materials such as cotton.
  • a paper or an overhead projector slide or textile material printed with an ink composition comprising a compound of Formula (1).
  • the solvent is preferably selected from ketones, alkanols, aliphatic hydrocarbons, esters, ethers, amides or mixtures thereof.
  • a polar solvent such as an alcohol, ester, ether or amide is preferably added.
  • Preferred solvents include ketones, especially methyl ethyl ketone and alkanols especially ethanol and n-propanol.
  • Solvent based ink compositions are used where fast drying times are required and particularly when printing onto hydrophobic substrates such as plastics, metal or glass.
  • the melting point of the solid is preferably in the range from 60°C to 125°C.
  • Suitable low melting point solids include long chain fatty acids or alcohols, preferably those with C 18 . 24 chains, or sulphonamides.
  • the compound of Formula (1) may be dissolved in the low melting point solid or may be finely dispersed in it.
  • a process for the coloration of a textile material with any of the abovementioned ink compositions comprising a compound of Formula (1 ) which comprises the steps :- i) applying to the textile material by inkjet printing the ink composition; and ii) heating the textile material at a temperature from 50°C to 250°C to fix the compound on the material.
  • the process for coloration of a textile material by inkjet printing preferably comprises a pre-treatment of the textile material with an aqueous pretreatment composition comprising a water-soluble base, a hydrotropic agent and a thickening agent followed by removing water from the pre-treated textile material to give a dry pre-treated textile material which is subjected to inkjet printing in step i) above.
  • the pretreatment composition preferably comprises a solution of the base and the hydrotropic agent in water containing the thickening agent.
  • the base is preferably an inorganic alkaline base, especially a salt of an alkali metal with a weak acid such as an alkali metal carbonate, bicarbonate or silicate or an alkali metal hydroxide.
  • the amount of base may be varied within wide limits provided sufficient base is retained on the textile material after pretreatment to promote the formation of a covalent bond between the compound and the pretreated textile material.
  • the base is sodium bicarbonate it is convenient to use a concentration of from 1% to 5% by weight based on the total weight of the composition.
  • the hydrotropic agent is present to provide sufficient water to promote the fixation reaction between the compound and the textile material during the heat treatment, in step (d) above, and any suitable hydrotropic agent may be employed.
  • Preferred hydrotropic agents are urea, thiourea and dicyandiamide.
  • the amount of hydrotropic agent depends to some extent on the type of heat treatment. If steam is used for the heat treatment generally less hydrotropic agent is required than if the heat treatment is dry, because the steam provides a humid environment.
  • the amount of hydrotropic agent required is generally from 2.5% to 50% by weight of the total composition with from 2.5% to 10% being more suitable for a steam heat treatment and from 20% to 40% being more suitable for a dry heat treatment.
  • the thickening agent may be any thickening agent suitable for use in the preparation of print pastes for the conventional printing of cellulose reactive dyes.
  • Suitable thickening agents include alginates, especially sodium alginate, xantham gums, monogalactam thickeners and cellulosic thickeners.
  • the amount of the thickening agent can vary within wide limits depending on the relationship between concentration and viscosity. However, sufficient agent is preferred to give a viscosity from 10 to 1000 mPa.s, preferably from 10 to 100 mPa.s, (measured on a Brookfield RVF Viscometer). For an alginate thickener this range can be provided by using from 10% to 20% by weight based on the total weight of the pretreatment composition.
  • the remainder of the pretreatment composition is preferably water, but other ingredients may be added to aid fixation of the compound to the textile material or to enhance the clarity of print by inhibiting the diffusion (migration) of compound from coloured areas to non-coloured areas before fixation.
  • fixation enhancing agents are cationic polymers, such as a 50% aqueous solution of a dicyanamide/phenol formaldehyde/ammonium chloride condensate e.g. MATEXIL FC-PN (available from ICI), which have a strong affinity for the textile material and the compound, even a compound which has been rendered unreactive by hydrolysis of the reactive group, and thus increase the fixation of the compound on the textile material.
  • a dicyanamide/phenol formaldehyde/ammonium chloride condensate e.g. MATEXIL FC-PN (available from ICI)
  • anti-migration agents are low molecular weight acrylic resins, e.g. polyacrylates, such as poly(acrylic acid) and poly(vinyl acrylate).
  • polyacrylates such as poly(acrylic acid) and poly(vinyl acrylate).
  • the compound of Formula (1) contains a monochloro-S-triazinyl reactive group
  • the yield of compound fixed to the textile material can be improved by the addition to the pretreatment composition of certain tertiary amines which are capable of interacting with the reactive group so as to replace the chloro atom and form a quaternary nitrogen leaving group, corresponding to the tertiary amine, which is displaced during fixation reaction of the compound with the textile material. It is therefore a preferred feature of the present process that the pretreatment composition also contains such a tertiary amine.
  • tertiary amine Any tertiary amine may be used, but a preferred tertiary amines are substantially odourless compounds such as 1 ,4-diazabicyclo[2.2.2]octane (DABCO) and substituted pyridines, preferably carboxypyridines, and especially those in which the pyridine ring is substituted by a carboxylic acid group in the 3 or 4 position, such as nicotinic or isonicotinic acid.
  • DABCO 1 ,4-diazabicyclo[2.2.2]octane
  • substituted pyridines preferably carboxypyridines, and especially those in which the pyridine ring is substituted by a carboxylic acid group in the 3 or 4 position, such as nicotinic or isonicotinic acid.
  • the pretreatment composition is preferably evenly applied to the textile material. Where a deeply penetrated print or a deep shade is required the pretreatment composition is preferably applied by a padding or similar process so that it is evenly distributed throughout the material. However, where only a superficial print is required the pretreatment composition can be applied to the surface of the textile material by a printing procedure, such as screen or roller printing, ink jet printing or bar application.
  • water may be removed from the pre-treated textile material by any suitable drying procedure such as by exposure to hot air or direct heating, e.g. by infra-red radiation, or micro-wave radiation, preferably so that the temperature of the material does not exceed 100°C.
  • the application of the ink composition to the textile material, stage (i) of the present process may be effected by any ink jet printing technique, whether drop on demand (DOD) or continuous flow.
  • the ink composition preferably also contains a humectant to inhibit evaporation of water and a preservative to inhibit the growth of fungi, bacteria and/or algae in the solution.
  • a humectant to inhibit evaporation of water and a preservative to inhibit the growth of fungi, bacteria and/or algae in the solution.
  • the reactive group is labile even in neutral environment
  • hydrolysis of the reactive group on the compound in the aqueous composition and during the fixation can be inhibited by use, as humectant, of a glycol or mixture of glycols, in which not more than one hydroxy group is a primary hydroxy group.
  • humectants examples include, propan-1 ,2-diol, butan-1 ,2-diol, butan-2,3-diol and butan-1,3-diol.
  • the presence of small amounts, up to about 10%, preferably not more than 5%, in total, of polyols having two or more primary hydroxy and/or primary alcohols is acceptable, although the composition is preferably free from such compounds.
  • the composition preferably also contains a conducting material such as an ionised salt to enhance and stabilise the charge applied to the drops.
  • Suitable salts for this purpose are alkali metal salts of mineral acids.
  • the ink composition After application of the ink composition, it is generally desirable to remove water from the printed textile material at relatively low temperatures ( ⁇ 100°C) prior to the heat applied to fix the compound on the textile material as this has been found to minimise the diffusion of the compound from printed to non-printed regions.
  • ⁇ 100°C relatively low temperatures
  • removal of water is preferably by heat, such as by exposure to hot air or to infra-red or micro-wave radiation.
  • the printed textile material is submitted to a short heat treatment, preferably after removal of water by low-temperature drying, at a temperature from 100°C to 200°C by exposure to dry or steam heat for a period of up to 20 minutes in order to effect reaction between the compound and the fibre and thereby to fix the compound on the textile material.
  • a steam (wet) heat treatment is used, the printed material is preferably maintained at 100-105°C for from 5 to 15 minutes whereas if a dry heat treatment is employed the printed material is preferably maintained at 140- 160°C for from 2 to 8 minutes.
  • unfixed compound and other ingredients of the pretreatment and ink compositions may be removed from the textile material by a washing sequence, involving a series of hot and cold washes in water and aqueous detergent solutions before the textile material is dried.
  • textile materials especially cellulosic textile materials, coloured with any of the ink compositions according to the present invention or by means of the process according to the present invention.
  • a toner resin composition comprising a toner resin and a compound characterised in that the compound is of Formula (1 ).
  • the toner resin is a thermoplastic resin suitable for use in the preparation of toner compositions.
  • a preferred toner resin is a styrene or substituted styrene polymer or copolymer such as polystyrene or styrene-butadiene copolymer, especially a styrene- acrylic copolymer such as a styrene-butyl methacrylate copolymer.
  • Other suitable toner resins include polyesters, polyvinylacetate, polyalkenes, polyvinylchloride, poiyurethanes, polyamides, siiicones, epoxyresins and phenolic resins. Examples of toner resins are given in Electrophotography by R.M.Scharfert (Focal Press), US 5143809, UK 2090008, US 4206064 and US 4407928.
  • the toner resin composition preferably contains from 0.1% to 20% of the compund of Formula (1) more preferably from 3% to 10% based on the total weight of the toner resin compositions.
  • the toner resin composition may be prepared by any method known to the art which typically involves mixing the toner resin with a charge control agent (CCA) and the compound of Formula (1) by kneading in a ball mill above the melting point of the resin. Generally, this involves mixing the molten toner resin composition for several hours at temperatures from 120 to 200°C, in order to uniformly distribute the CCA and compound throughout the toner resin. The toner resin is then cooled, crushed and micronised until the mean diameter of the particles is preferably below 20 ⁇ m and, for high resolution electro-reprography, more preferably from 1 to 10 ⁇ m.
  • CCA charge control agent
  • the powdered toner resin composition so obtained may be used directly or may be diluted with an inert solid diluent such as fine silica by mixing for example in a suitable blending machine.
  • CCA's are more fully described in WO94/23344.
  • the invention is further illustrated by the following Examples, which may be used to prepare ink compositions of the present invention, in which all parts and percentages are by weight unless otherwise stated.
  • Example 2 The procedure as described above for Example 1 was followed except that the aniline was replaced with N-ethyianiline, the 3-chloropropan-1-ol was replaced with ethyl 4- bromobutyrate and the 2-(4-aminophenyl)ethanol was replaced with 4-aminophenylacetic acid and the product was hydrolysed with sodium hydroxide in methanol to give the title compound m.p. 147-148°C.
  • Example 2 The procedure as described above for Example 2 was followed except that the ethyl 4- bromobutyrate was replaced with 4-bromobutan-1-ol to give the title compound m.p.105- 107°C.
  • Example 8 The product from Example 8 (2.4g) was dissolved in warm methanol (25cm 3 ) and aqueous sodium hydroxide (40%w/w, 1.5cm 3 ) added dropwise. The resulting paste was poured into water (100cm 3 ), cooled to room temperature and the dark solution acidified with hydrochloric acid giving a yellow precipitate which was filtered off and washed with water before air drying. Traces of impurities were removed by slurrying in hot ethyl acetate. On filtering and washing with ethyl acetate a pure product was obtained (94%) mp 189-92°C.
  • 3-(3-Aminophenyl)propionic acid 3-Nitrocinnamic acid 50g was suspended in ethanol (600cm 3 ) and reduced in the presence of palladium catalyst until no further hydrogen uptake was observed. After filtering the solvent was evaporated under reduced pressure to give the pure product in quantitative yield as a brown oil which slowly crystallised.
  • 3-(3-Aminophenyl)propionic acid (0.83g) was added to a solution of hydrochloric acid (3cm 3 ) in water (20cm 3 ) at 0°C. A solution of sodium nitrite (0.35g) in the minimum of water was then added dropwise keeping the temperature below 5°C.
  • N,N-bis(3-hydroxypropyl) aniline (10.46g) was dissolved in hydrochloric acid (20cm 3 ) at 0-5°C and sodium nitrite(3.45g) in water(15cm 3 ) was added dropwise. The mixture was stirred for 1hr, water (10cm 3 ) was added, made alkaline with sodium carbonate, separated in to an oil and water layer. The oil was dissolved in dichloromethane and the solvent removed to leave N,N-bis(3-hydroxypropyl)-4- nftrosoaniline as a yellow solid.
  • Example 21 The procedure as described in Example 19 above was followed,except that the aniline was replaced with 2-aminoacetanilide (42.23g) to leave the title compound m.p. 230-232°C, ⁇ max 644nm, ⁇ max 38299
  • 2-aminoacetanilide 42.23g
  • Example 2 The procedure as described for Example 1 was followed except that the 3- chloropropan-1-ol was replaced with 5-chloropentan-1-ol to give the title compound m.p.68-70°C, ⁇ max 416nm (ethyl acetate), ⁇ max 31354
  • Example 2 The procedure as described for Example 1 was followed except that the 3- chloropropan-1-ol was replaced by 7-bromoheptan-1-ol to give the title compound ⁇ max 416nm (ethyl acetate), ⁇ max 30641.
  • Example 2 The procedure as described for Example 2 was followed except that the ethyl-4- bromobutyrate was replaced with the chloropropan-1-ol and the 2-(4-aminophenyl)acetic acid was replaced with 2-(4-aminophenyl) ethanol to give the title compound ⁇ max 414nm (ethyl acetate), ⁇ max 35656.
  • Example 2 The procedure as described above for Example 1 was followed .except that the 3- chloropropan-1-ol was replaced with acrylamide and the 2-(4-aminophenyl)ethanol was replaced with aniline to give the title compound m.p.171-175°C, ⁇ max 404nm (ethyl acetate), ⁇ max 26932.
  • 4-Nitroaniiine (4.2g) was added portionwise with stirring to a mixture of acetic acid (200cm 3 ), propionic acid (9cm 3 ) and nitrosyl sulphuric acid 40%w/w (10cm 3 ) at 0-5°C. The mixture was stirred for 1 hr. The resulting solution was added with stirring to a solution of N,N-diaminopropylaniline (6.2g) and sulphamic acid (1g) in methanol (200cm 3 ) at 0-5°C, stirred for 1 hr, diluted with water (300cm 3 ) to give the title compound mp 130- 132°C, ⁇ max 462nm (acetone).
  • 4-Aminophenyl-2-sulphatoethylsulphone (5.8g) was added portionwise with sti ⁇ ing to a mixture of concentrated hydrochloric acid (20cm 3 ), in water (180cm 3 ) at 0-5°C and sodium nitrite (1.52g) in water (200cm 3 ) was added dropwise. The mixture was stirred for 1 hr and the excess nitrous acid destroyed by the addition of sulphamic acid.
  • Example 12 The procedure as described for Example 12 was followed except the 4-(4-cyano- 3-methylisothiazol-5-ylazo)-N-N-bis(2-hydroxyethyl)-3-toluidine was replaced by 4-(4- ethylhydroxyphenylazo)-N-N-bis(2-hydroxyethyl)-3-aminoacetanilide to give the title compound, ⁇ max 464nm (water).
  • Example 12 The procedure as described for Example 12 was followed except the 4-(4-cyano- 3-methylisothiazol-5-ylazo)-N-N-bis(2-hydroxyethyl)-3-toluidine was replaced with 4-(4- ethyIhydroxyphenylazo)-N-secbutyl-N-carboxyethyl)-3-toluidine to give the title compound, mp 140-142°C, ⁇ max 416nm (methanol).
  • the diazonium salt solution was then added to a cooled solution of 3-(N,N-bis-3- hydroxypropylamino)acetanilide (5.32g, 0.02mole) in methanol (100cm 3 ) to which sodium acetate (5.7g) was diluted with water (250cm 3 ) and the orange product filtered off washed well with water and dried in a vacuum oven at 60°C. Yield 8.29g (72.4%).
  • p-Nitrobenzenediazonium fluoroborate (1.18g, 4.98mole) was dissolved in a water- acetone mixture and filtered into a solution of diethyl (3-N,N-di-n-butylaminobenzyl) malonate (1.85g, 4.9mole) in methanol (30cm 3 ). After sti ⁇ ing for a further 30mins the mixture was diluted with water (100cm 3 ) and allowed to stand over the weekend. The sticky solid was filtered off and washed with water. Sample was purified by column chromotography on silica gel to give the title compound (1.82g, 69.4%).
  • Example 53 The azo diester from Example 51 (1.5g) was dissolved in methanol (30cm 3 ) the aid of gentle warming and caustic liquor (ca 48% w/w 10 drops) added with stirring. After 15mins TLC showed no azo diester remaining. The solution was poured onto ice (150g) and the slurry obtained was acidified by the addition of hydrochloric acid. The resulting dark red solid was filtered off and washed well with water before air drying. The solid was purified by column chromatography on silica gel using 8% v/v methanol in dichloromethane to give the title compound (0.29g).
  • Example 53 Preparation of

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet (AREA)

Abstract

Composés et compositions d'encre. Composition d'encre qui comprend un composé de formule (I) et des sels dudit composé. Dans ladite formule, Ch représente une disposition d'atomes qui pousse ledit composé à absorber des rayons électromagnétiques, Ra et Rb sont chacun indépendamment un groupe d'espacement, Y est un groupe fonctionnel interactif, w et x sont chacun indépendamment 0 ou un nombre entier supérieur à 1 et m et n sont chacun indépendamment un nombre entier égal ou supérieur à 1, à condition que w et x ne soient pas tous les deux égaux à zéro et que lorsque w ou x est 0, au moins m ou n soit égal ou supérieur à 2. Ladite composition est destinée à être utilisée dans l'impression à jet d'encre et l'électrophotographie.
PCT/GB1996/000994 1995-05-01 1996-04-26 Composition d'encre WO1996034916A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP96911052A EP0823927A2 (fr) 1995-05-01 1996-04-26 Composition d'encre
JP8533099A JPH11504958A (ja) 1995-05-01 1996-04-26 化合物
US08/945,649 US6099625A (en) 1995-05-01 1996-04-26 Ink composition

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9508810.0 1995-05-01
GBGB9508810.0A GB9508810D0 (en) 1995-05-01 1995-05-01 Compounds
GBGB9508874.6A GB9508874D0 (en) 1995-05-02 1995-05-02 Compounds
GB9508874.6 1995-05-02

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JP (1) JPH11504958A (fr)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000027928A1 (fr) * 1998-11-09 2000-05-18 Nippon Kayaku Kabushiki Kaisha Composition pour teinture, composition pour encre et technique d'impression par jet d'encre
JP2001512776A (ja) * 1997-08-12 2001-08-28 キャボット コーポレイション 遊離性基を有するインクとコーティング用の改質炭素生産品
US6489452B1 (en) 2000-03-22 2002-12-03 Fuji Photo Film Co., Ltd. Azo dyes, process for making the same, ink-jet printing ink, ink-jet recording method
WO2003062330A1 (fr) * 2002-01-25 2003-07-31 Fuji Photo Film Co., Ltd. Encre pour impression par jet d'encre, jeu d'encres pour impression par jet d'encre, et procede d'impression par jet d'encre
WO2003066757A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre destinee a l'impression jet d'encre et procede d'impression jet d'encre
WO2003066753A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre d'impression a jet d'encre et procede d'impression a jet d'encre
WO2003066756A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre et ensembles d'encre pour impression a jet d'encre et procede d'impression a jet d'encre
WO2003066754A1 (fr) * 2002-02-07 2003-08-14 Fuji Photo Film Co., Ltd. Encre pour impression par jet d'encre et procede d'impression par jet d'encre
WO2003068873A1 (fr) * 2002-02-13 2003-08-21 Fuji Photo Film Co., Ltd. Encre pour enregistrement par jet d'encre et procede d'enregistrement par jet d'encre
WO2003068872A1 (fr) * 2002-02-13 2003-08-21 Fuji Photo Film Co., Ltd. Encre pour impression a jet d'encre et procede d'impression correspondant
WO2003082994A1 (fr) * 2002-03-28 2003-10-09 Fuji Photo Film Co., Ltd. Ensemble d'encres pour l'enregistrement a jet d'encre et procede d'enregistrement a jet d'encre
EP1462494A1 (fr) * 2003-03-26 2004-09-29 Fuji Photo Film Co., Ltd. Encre et ensemble d'encres
US7201477B2 (en) 2001-04-09 2007-04-10 Fujifilm Corporation Ink for ink jet recording, ink set for ink jet recording and ink jet recording method
EP2362890A2 (fr) * 2008-10-27 2011-09-07 Life Technologies Corporation Composes a base d'anthraquinone emettant un infrarouge proche et utilisations associees

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EP1473332B1 (fr) * 2002-02-04 2011-05-25 FUJIFILM Corporation Composition d'encre et procede d'impression par jet d'encre
DE60328660D1 (de) * 2002-02-08 2009-09-17 Fujifilm Corp Tintenstrahlaufzeichnungstinte und tintenstrahlaufzeichnung
JP4226860B2 (ja) * 2002-08-22 2009-02-18 富士フイルム株式会社 インクセット、インクカートリッジ、記録方法、プリンター及び記録物
JP4486831B2 (ja) 2003-03-31 2010-06-23 富士フイルム株式会社 インクセットならびにインクジェット記録方法
JP2007510760A (ja) 2003-10-02 2007-04-26 富士フイルム株式会社 インクジェット用インク、インクジェット用インクセットならびにインクジェット記録方法
US7923083B2 (en) 2004-03-11 2011-04-12 Fujifilm Corporation Recording medium, ink composition and recording method using the same
JP2006016457A (ja) 2004-06-30 2006-01-19 Fuji Photo Film Co Ltd インク組成物、インクセット、インクジェット記録用インク、インクジェット記録用インクセット、並びにインクジェット記録用インクカートリッジ
JP4512507B2 (ja) * 2004-07-09 2010-07-28 富士フイルム株式会社 ピリドンアゾ化合物およびこの互変異性体を含み着色剤含有硬化性組成物、カラーフィルタおよびその製造方法
JP2007204632A (ja) 2006-02-02 2007-08-16 Fujifilm Corp インク組成物およびこれを用いる記録方法
JP2014185286A (ja) * 2013-03-25 2014-10-02 Nitto Denko Corp ベンゾトリアゾール構造を有する発色団およびそれを用いた波長変換発光媒体

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EP0330487A2 (fr) * 1988-02-26 1989-08-30 MITSUI TOATSU CHEMICALS, Inc. Composition d'agent de contraste coloré
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GB224363A (en) * 1923-10-25 1924-11-13 British Dyestuffs Corp Ltd New dyestuffs of the anthraquinone series
FR2208791A1 (fr) * 1972-12-01 1974-06-28 Agfa Gevaert Ag
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EP0196901A2 (fr) * 1985-03-29 1986-10-08 Taoka Chemical Co., Ltd Composé de phtalocyanine de cuivre et composition aqueuse d'encre comprenant un tel composé
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EP0330487A2 (fr) * 1988-02-26 1989-08-30 MITSUI TOATSU CHEMICALS, Inc. Composition d'agent de contraste coloré
EP0441255A2 (fr) * 1990-02-03 1991-08-14 Orient Chemical Industries, Ltd. Dérivé de dicyanoimidazole, toner magenta, résine colorée, élément façonné en résine colorée et filtre couleur le comprenant
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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001512776A (ja) * 1997-08-12 2001-08-28 キャボット コーポレイション 遊離性基を有するインクとコーティング用の改質炭素生産品
WO2000027928A1 (fr) * 1998-11-09 2000-05-18 Nippon Kayaku Kabushiki Kaisha Composition pour teinture, composition pour encre et technique d'impression par jet d'encre
US6613888B2 (en) 2000-03-22 2003-09-02 Fuji Photo Film Co., Ltd. Azo dyes, process for making the same, ink-jet printing ink, ink-jet recording method
US6489452B1 (en) 2000-03-22 2002-12-03 Fuji Photo Film Co., Ltd. Azo dyes, process for making the same, ink-jet printing ink, ink-jet recording method
US7201477B2 (en) 2001-04-09 2007-04-10 Fujifilm Corporation Ink for ink jet recording, ink set for ink jet recording and ink jet recording method
WO2003062330A1 (fr) * 2002-01-25 2003-07-31 Fuji Photo Film Co., Ltd. Encre pour impression par jet d'encre, jeu d'encres pour impression par jet d'encre, et procede d'impression par jet d'encre
US7316472B2 (en) 2002-02-07 2008-01-08 Fujifilm Corporation Jet printing ink and method of ink jet printing
WO2003066754A1 (fr) * 2002-02-07 2003-08-14 Fuji Photo Film Co., Ltd. Encre pour impression par jet d'encre et procede d'impression par jet d'encre
US7291212B2 (en) 2002-02-08 2007-11-06 Fujifilm Corporation Ink and ink set for ink jet printing and method of ink jet printing
WO2003066756A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre et ensembles d'encre pour impression a jet d'encre et procede d'impression a jet d'encre
US7390083B2 (en) 2002-02-08 2008-06-24 Fujifilm Corporation Ink-jet recording ink and method of ink-jet recording
WO2003066757A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre destinee a l'impression jet d'encre et procede d'impression jet d'encre
WO2003066753A1 (fr) * 2002-02-08 2003-08-14 Fuji Photo Film Co., Ltd. Encre d'impression a jet d'encre et procede d'impression a jet d'encre
US7287848B2 (en) 2002-02-08 2007-10-30 Fujifilm Corporation Ink for inkjet recording and method for inkjet recording
US7175268B2 (en) 2002-02-13 2007-02-13 Fuji Photo Film Co., Ltd. Inkjet recording ink and inkjet recording method
US7249834B2 (en) 2002-02-13 2007-07-31 Fujifilm Corporation Inkjet recording ink and inkjet recording method
WO2003068872A1 (fr) * 2002-02-13 2003-08-21 Fuji Photo Film Co., Ltd. Encre pour impression a jet d'encre et procede d'impression correspondant
WO2003068873A1 (fr) * 2002-02-13 2003-08-21 Fuji Photo Film Co., Ltd. Encre pour enregistrement par jet d'encre et procede d'enregistrement par jet d'encre
US7198362B2 (en) 2002-03-28 2007-04-03 Fuji Photo Film Co., Ltd. Ink set for ink-jet recording and ink-jet recording method
WO2003082994A1 (fr) * 2002-03-28 2003-10-09 Fuji Photo Film Co., Ltd. Ensemble d'encres pour l'enregistrement a jet d'encre et procede d'enregistrement a jet d'encre
EP1462494A1 (fr) * 2003-03-26 2004-09-29 Fuji Photo Film Co., Ltd. Encre et ensemble d'encres
EP2362890A2 (fr) * 2008-10-27 2011-09-07 Life Technologies Corporation Composes a base d'anthraquinone emettant un infrarouge proche et utilisations associees
EP2362890A4 (fr) * 2008-10-27 2012-10-24 Life Technologies Corp Composes a base d'anthraquinone emettant un infrarouge proche et utilisations associees
US8999965B2 (en) 2008-10-27 2015-04-07 Life Technologies Corporation Anthraquinone based near IR emitting compounds and uses thereof
US9709557B2 (en) 2008-10-27 2017-07-18 Life Technologies Corporation Anthraquinone based near IR emitting compounds and uses thereof

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WO1996034916A3 (fr) 1997-01-03
JPH11504958A (ja) 1999-05-11

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