US20020128488A1 - Azomethine compound and oily magenta ink - Google Patents

Azomethine compound and oily magenta ink Download PDF

Info

Publication number
US20020128488A1
US20020128488A1 US10/095,448 US9544802A US2002128488A1 US 20020128488 A1 US20020128488 A1 US 20020128488A1 US 9544802 A US9544802 A US 9544802A US 2002128488 A1 US2002128488 A1 US 2002128488A1
Authority
US
United States
Prior art keywords
carbon atoms
group
cyano
azomethine compound
alkyl group
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.)
Abandoned
Application number
US10/095,448
Other languages
English (en)
Inventor
Katsuyoshi Yamakawa
Masuji Motoki
Naoki Asanuma
Ryo Suzuki
Tadahisa Sato
Hisashi Mikoshiba
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.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
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
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Priority to US10/095,448 priority Critical patent/US20020128488A1/en
Publication of US20020128488A1 publication Critical patent/US20020128488A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • the present invention relates to an azomethine compound.
  • the invention relates to an azomethine compound suitable for a jet printing ink of magenta color.
  • an ink-jet recording method images or characters are printed on image-receiving material with ink ejected from very fine nozzles.
  • the ink-jet recording method can be conducted by using a relatively inexpensive apparatus (i.e., an ink-jet printer), as compared with other printing methods. Further, in proportion to improvement of the method, images of high qualities have been given recently. Now, the ink-jet recording method is one of the most popular image-recording methods.
  • Ink for the ink-jet recording method i.e., jet printing ink
  • aqueous inks aqueous solutions of dyes
  • the aqueous inks have poor water resistance.
  • Various means (described in Japanese Patent Provisional Publication Nos. 4(1992)-28776, 4(1992)-189876, 4(1992)-261478, 4(1992)-359071 and 4(1992)-359072) have been proposed to improve the water resistance of the aqueous inks or water-soluble dyes.
  • the water-soluble dyes have poor light resistance.
  • Oil-soluble dyes (described in Japanese Patent Provisional Publication Nos. 1(1989)-170672, 3(1991)-221137, 7(1995)-96163, 8(1996)-218015, 9(1997)-3376, 9(1997)-241565, 9(1997)-286939 and 10(1998)-279873) have been proposed in place of the water-soluble dyes.
  • the oil-soluble dyes are usually incorporated in microcapsules or soaked in polymers when they are used for ink-jet printing. Although the oil-soluble dyes have satisfying water resistance, they are unsatisfactory in color reproduction and color stability.
  • Water-soluble dyes for ink-jet recording have poor resistance against water and light, while oil-soluble dyes are unsatisfactory in color reproduction and color stability.
  • An object of the present invention is to provide an oil-soluble dye excellent in color reproduction and color stability.
  • Another object of the invention is to provide an azomethine compound suitable for a jet printing ink of magenta color.
  • a further object of the invention is to provide an oily magenta ink for ink-jet recording.
  • the applicants have found an azomethine compound having light-absorption characteristics suitable for a magenta dye.
  • the compound is oil-soluble, and is advantageously used in a preparation of an oily magenta ink for ink-jet recording.
  • the present invention provides an azomethine compound represented by the formula (I):
  • R 1 is an alkyl group having 1 to 16 carbon atoms
  • R 2 is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano
  • R 3 is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having 3 to 30 carbon atoms
  • R 4 is an alkyl group having 1 to 16 carbon atoms
  • L l is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms
  • L 2 is —CO—NH—, —SO 2 —NH—, —O—, —O—CO—or —O—CO
  • the invention also provides an oily magenta ink in which an azomethine dye represented by the formula (I) is dissolved in an organic solvent.
  • the azomethine compound represented by the formula (I) has excellent characteristics suitable for a magenta dye. Accordingly, the azomethine compound can be advantageously used in a preparation of an oily magenta ink for ink-jet recording.
  • the azomethine compound represented by the formula (I) is excellent in stability to light and heat. Accordingly, the azomethine compound can be used a magenta dye that is excellent in a light resistance and in a heat resistance.
  • the azomethine compound represented by the formula (I) can be classified into the three embodiments represented by the formulas (I a ), (I b ) and (I c ), respectively.
  • the embodiment of the formula (I a ) is particularly preferred.
  • R 1 is an alkyl group having 1 to 16 carbon atoms.
  • the alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 6 carbon atoms, and most preferably has 1 to 4 carbon atoms.
  • the alkyl group can have a branched chain. Examples of the alkyl groups include methyl and t-butyl.
  • R 2 is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano.
  • the alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 1 or 2 carbon atoms.
  • the alkyl group can have a branched chain. Examples of the alkyl groups include methyl and ethyl.
  • the alkoxy group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 1 or 2 carbon atoms.
  • the alkoxy group can have a branched chain. Examples of the alkoxy groups include methoxy.
  • the amido group preferably has 2 to 12 carbon atoms, more preferably has 2 to 8 carbon atoms, further preferably has 2 to 6 carbon atoms, and most preferably has 3 or 4 carbon atoms.
  • Examples of the amido groups include acetamido.
  • the alkoxycarbonylamino group preferably has 2 to 12 carbon atoms, more preferably has 2 to 8 carbon atoms, further preferably has 2 to 6 carbon atoms, and most preferably has 2 or 3 carbon atoms.
  • Examples of the alkoxycarbonylamino groups include methoxycarbonylamino.
  • R 3 is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxylcarbonylalkyl group having 3 to 30 carbon atoms.
  • the alkyl group preferably has 2 to 25, more preferably has 3 to 20 carbon atoms, and most preferably has 4 to 16 carbon atoms.
  • the alkyl group can have a branched chain.
  • Examples of the aryl groups include phenyl and naphthyl. Phenyl is preferred.
  • the aryl group can have a substituent group.
  • Examples of the substituent groups include a halogen atom, an alkyl group having 1 to 24 carbon atoms and an alkoxy group having 1 to 24 carbon atoms.
  • the aryl group has 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 16 carbon atoms.
  • the number of the carbon atoms means the number of the total carbon atoms contained in the aryl group and the substituent group.
  • the alkyl moiety of the aryloxyalkyl group can have a branched chain.
  • the aryl moiety of the aryloxyalkyl group is preferably phenyl.
  • the aryloxyalkyl group can have a substituent group. Examples of the substituent groups include a halogen atom, an alkyl group having 1 to 23 carbon atoms and an alkoxy group having 1 to 23 carbon atoms.
  • the aryloxyalkyl group has 7 to 30 carbon atoms, preferably has 7 to 25 carbon atoms, more preferably 7 to 20 carbon atoms, and further preferably 7 to 16 carbon atoms.
  • the number of the carbon atoms means the number of the total carbon atoms contained in the aryloxyalkyl group and the substituent group.
  • the alkoxycarbonylalkyl group preferably has 3 to 25 carbon atoms, more preferably has 4 to 20 carbon atoms, and most preferably has 5 to 16 carbon atoms.
  • Each of the two alkyl moieties of the alkoxycarbonylalkyl group can have a branched chain.
  • R 4 is an alkyl group having 1 to 16 carbon atoms.
  • the alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 6 carbon atoms, and most preferably has 1 to 4 carbon atoms.
  • the alkyl group can have a branched chain. Examples of the alkyl groups include methyl and ethyl.
  • L 1 is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms.
  • the alkylene group preferably has 1 to 25 carbon atoms, more preferably has 2 to 20 carbon atoms, and most preferably has 2 to 16 carbon atoms.
  • the alkylene group can have a branched chain.
  • Examples of the arylene groups include phenylene and naphthylene. Phenylene is preferred.
  • the arylene group can have a substituent group. Examples of the substituent groups include a halogen atom, an alkyl group having 1 to 24 carbon atoms and an alkoxy group having 1 to 24 carbon atoms.
  • the arylene group has 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 16 carbon atoms. The number of the carbon atoms means the number of the total carbon atoms contained in the arylene group and the substituent group.
  • L 2 is —CO—NH—, —SO 2 —NH—, —O—, ——O—CO—or —O—CO—NH—, in each of which the left side is attached to R 3 , and the right side is attached L 1 .
  • X is cyano, an alkoxy-carbonyl group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or an arylsulfamoyl group having 6 to 26 carbon atoms. Cyano and an alkoxycarbonyl group having 2 to 19 carbon atoms are preferred, and cyano is most preferred.
  • the alkoxycarbonyl group preferably has 2 to 8 carbon atoms.
  • Examples of the alkoxycarbonyl groups include methoxycarbonyl and dodecyloxycarbonyl.
  • the alkylsulfonyl group preferably has 1 to 7 carbon atoms.
  • Examples of the alkylsulfonyl groups include methanesulfonyl.
  • the aryl moiety of the arylsulfonyl group is preferably phenyl.
  • the arylsulfonyl group can have a substituent group.
  • the substituent groups include a halogen atom, an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms.
  • the arylsulfonyl group has 6 to 26 carbon atom, and preferably has 6 to 15 carbon atoms.
  • the number of the carbon atoms means the number of the total carbon atoms contained in the arylsulfonyl group and the substituent group.
  • the arylsulfonyl groups include benzenesulfonyl.
  • the alkylsulfamoyl group preferably has 1 to 9 carbon atoms.
  • Examples of the alkylsulfamoyl groups include methylsulfamoyl.
  • the aryl moiety of the arylsulfamoyl group is preferably phenyl.
  • the arylsulfamoyl group can have a substituent group.
  • the substituent groups include a halogen atom, an alkyl group having 1 to 20 carbon atoms and an alkoxy group having 1 to 20 carbon atoms.
  • the arylsulfamoyl group has 6 to 26 carbon atoms, and preferably has 6 to 15 carbon atoms.
  • the number of the carbon atoms means the number of the total carbon atoms contained in the arylsulfamoyl group and the substituent group.
  • the arylsulfamoyl groups include phenylsulfamoyl.
  • Y is hydrogen, a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms. Hydrogen atom is particularly preferred.
  • the alkoxy group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 1 or 2 carbon atoms.
  • the alkoxy group can have a branched chain. Examples of the alkoxy groups include methoxy and ethoxy.
  • the aryl moiety of the aryloxy group is preferably phenyl.
  • the aryloxy group can have a substituent group.
  • the substituent groups include a halogen atom, an alkyl group having 1 to 14 carbon atoms and an alkoxy group having 1 to 14carbon atoms.
  • the aryloxy group has 6 to 20 carbon atoms, and preferably has 6 to 15 carbon atoms.
  • the number of the carbon atoms means the number of the total carbon atoms contained in the aryloxy group and the substituent group.
  • Examples of the aryloxy groups include phenoxy.
  • the acyloxy group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 2 or 3 carbon atoms.
  • Examples of the acyloxy groups include acetoxy.
  • m is an integer of 1 to 4, preferably is an integer of 1 to 3, and more preferably is 1 or 2.
  • (CH 2 ) m means an alkylene group of a straight chain.
  • n is an integer of 1 to 18, preferably is an integer of 1 to 14, more preferably is an integer of 1 or 10, further preferably is an integer of 1 to 8, and most preferably is an integer of 1 to 6.
  • the alkylene group represented by C n H 2n can have a branched chain.
  • p is 0, 1, 2, 3 or 4, preferably is 0, 1, 2 or 3, more preferably is 0, 1 or 2, further preferably is 0 or 1, and most preferably is 0.
  • the groups represented by R 2 can be different from each other.
  • R 1 , L 1 , L 2 and R 3 have 20 to 50 carbon atoms in total.
  • R 1 , L 1 , L 2 , R 3 and R 4 have 20 to 50 carbon atoms in total.
  • the total number of the carbon atoms preferably is 25 to 45.
  • the azomethine compound of the formula (I) preferably has a molecular weight of 600 to 2,000, and more preferably has a molecular weight of 800 to 1,500.
  • R 1 CH 3 , R 21 : H, R 22 : H,
  • R 3 1-(2,4-di-t-pentylphenoxy)heptyl
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • X cyano
  • R 1 CH 3 , R 21 : H, R 22 : H,
  • R 3 2-octyloxy-5-t-octylphenyl
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —SO 2 —NH—
  • X cyano
  • R 1 CH 3 , R 21 : H, R 22 : H,
  • R 3 2-octyloxy-5-(2-octyloxy-5-t-octylphenylsulfone-amido)phenyl,
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —SO 2 —NH—
  • X cyano
  • R 1 CH 3 , R 21 : H, R 22 : H,
  • R 3 2-tetradecyloxycarbonylethyl
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • R 1 CH 3 , R 21 : CH 3 , R 22 : H, R 3 : pentadecyl,
  • L 1 -1,4-phenylene-
  • L 2 —CO—NH—
  • X cyano
  • R 1 CH 3 , R 21 : CH 3 , R 22 : H,
  • R 3 1-(2,4-di-t-pentylphenoxy)heptyl
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • X cyano
  • R 1 CH 3 , R 21 : H, R 22 : H, R 3 : octadecyl,
  • L 1 —CH2—CH2—
  • L 2 —O—
  • X methoxycarbonyl
  • R 1 CH 3 , R 21 : H, R 22 : H, R 3 : hexadecyl,
  • L 1 -1,3-phenylene-
  • L 2 —O—CO—
  • X cyano
  • R 1 t—C 4 H 9 , R 21 : H, R 22 : H,
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • X cyano
  • R 1 t—C 4 H 9 , R 21 : H, R 22 : H,
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —SO 2 —NH—
  • X cyano
  • R 1 t—C 4 H 9
  • R 21 H
  • R 22 H
  • R 3 tridecyl
  • L 1 -1,3-phenylene-
  • L 2 —CO—NH—
  • X cyano
  • R 1 t—C 4 H 9 , R 21 : H, R 22 : H,
  • L 1 -1,4-phenylene-
  • L 2 —CO—NH—
  • X cyano
  • R 1 t—C 4 H 9 , R 21 : H, R 22 : H,
  • R 1 t—C 4 H 9 , R 21 : H, R 22 : H,
  • L 1 -1,4-phenylene-
  • L 2 —CO—NH—
  • X cyano
  • R 1 t—C 4 H 9 , R 21 : CH 3 , R 22 : H,
  • R 1 t—C 4 H 9 , R 21 : CH 3 , R 22 : H,
  • R 1 t—C 4 H 9 , R 21 : CH 3 , R 22 : H, R 3 : heptadecyl,
  • L 1 -1,2-phenylene-
  • L 2 —CO—NH—
  • R 1 t—C 4 H 9
  • R 21 NHCOCH 3
  • R 22 H
  • R 3 hexadecyl
  • L 1 -1,3-phenylene-
  • L 2 —SO 2 —NH—
  • X cyano
  • Y acetoxy
  • R 1 t—C 4 H 9 , R 21 OCH 3 , R 22 : H,
  • R 3 octadecyl
  • L 1 -1,4-phenylene-
  • L 2 —O—
  • X sulfamoyl
  • Y phenoxy
  • R 1 t—C 4 H 9
  • R 21 H
  • R 22 OCH 3
  • R 3 hexadecyl
  • L 1 -3-chloro-1,4-phenylene-
  • L 2 —O—
  • X methanesulfonyl
  • Y methoxy
  • R 1 C 2 H 5 , R 21 : H, R 22 : H, R 3 : pentadecyl,
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • X cyano
  • R 1 C 3 H 7 , R 21 : H, R 22 : H, R 3 : pentadecyl,
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • X cyano
  • R 1 C 7 H 15 , R 21 : CH 3 , R 22 : H,
  • R 1 C 4 H 9 , R 21 H, R 22 : H,
  • L 1 -1,4-phenylene-
  • L 2 —CO—NH—
  • R 1 C 3 H 7 , R 21 : H, R 22 : H,
  • R 1 C 2 H 5 , R 21 : H, R 22 : H,
  • L 1 -1,4-phenylene-
  • L 2 —CO—NH—
  • L 1 -1,3-phenylene-
  • L 2 —CO—NH—
  • R 1 CH 3
  • R 2 CH 3
  • R 3 tetradecyl
  • L 1 -3-chloro-1,4-phenylene-
  • L 2 —O—
  • R 1 CH 3
  • R 2 NHCO 2 CH 3
  • R 3 hexadecyl
  • L 1 -1,2-phenylene-
  • L 2 —O—
  • R 1 CH 3
  • R 2 CN
  • R 3 pentadecyl
  • L 1 —CH 2 —CH(CH 3 )—
  • L 2 —CO—NH—
  • R 1 CH 3
  • R 3 heptadecyl
  • R 4 CH 3
  • R 1 t—C 4 H 9
  • R 3 2-tetradecyloxycarbonylethyl
  • R 4 C 2 H 5 , L 1 : -1,4-phenylene-,
  • the azomethine compound of the formula (I) can be synthesized by referring to the method described in Japanese Patent Provisional Publication No. 4(1992)-126772.
  • the azomethine compound can be synthesized by a reaction of an azole compound represented by the formula (II) with a p-phenylenediamine compound represented by the formula (III) under an oxidizing condition.
  • Z 1 , Z 2 , R 1 , R 2 , X, Y, m, n and p are the same as those described above for the formula (I); and R is a group eliminable in the reaction.
  • the eliminable groups (R) include hydrogen, a halogen atom, a heterocyclic group and an aryloxy group.
  • an anti-fading agent can further improve its light resistance.
  • the anti-fading agent is described in “Shikizai (written in Japanese)”, 797, 70(1997).
  • Particularly preferred examples of the anti-fading agents are spirochroman and spiroindane.
  • the azomethine compound of the formula (I) is preferably used as a magenta dye, particularly an oily magenta ink suitably used for ink-jet recording.
  • the oily magenta ink for ink-jet recording can be easily prepared according to known publications (for example, Japanese Patent Provisional Publication Nos. 3(1991)-231975, 11(1999)-158422, 11(1999)-172183).
  • Organic solvents employable for preparing the oily magenta ink are hydrocarbons, alcohols, ketones, ethers, esters, nitriles, amides, sulfoxides and sulfones. Esters and ketones are particularly preferred.
  • hydrocarbons examples include petroleum ether, petroleum benzine, tetralin, decalin, 1-amylbenzene and methylnaphthalene.
  • Examples of the alcohols include ethanol, pentanol, heptanol, octanol, cyclohexanol, benzyl alcohol, phenyl-ethyl alcohol, phenylpropyl alcohol, anise alcohol, ethylene glycol monoethyl ether, ethylene glycol monophenyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monoethyl ether, propylene glycol monophenyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether and tripropylene glycol monoethyl ether.
  • ketones examples include methyl ethyl ketone, benzyl methyl ketone, diacetone alcohol and cyclohexanone.
  • ethers examples include butyl phenyl ether, benzyl ethyl ether and hexyl ether.
  • esters examples include ethyl acetate, amyl acetate, benzyl acetate, phenylethyl acetate, phenoxyethyl acetate, ethyl phenylacetate, benzyl propionate, ethyl benzoate, butyl benzoate, ethyl laurate, butyl laurate, isopropyl myristate, isopropyl palmitate, triethyl phosphate, tributyl phosphate, diethyl phthalate, diethyl malonate, dipropyl malonate, diethyl diethylmalonate, diethyl succinate, dibutyl succinate, diethyl glutarate, diethyl adipate, dibutyl adipate, di(2-methoxyethyl) adipate, diethyl sebacate, diethyl maleate, dibutyl maleate, dibuty
  • nitriles examples include acetonitrile.
  • amides examples include formamide, N,N-di-methylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone and N,N-diethyldodecaneamide.
  • Examples of the sulfoxides include dimethyl sulfoxide.
  • Examples of the sulfones include sulfolane.
  • Two or more organic solvents can be used in combination.
  • the oily magenta ink contains the azomethine compound preferably in an amount of 0.2 to 20 wt. %, and more preferably in an amount of 0.5 to 10 wt. %.
  • the ink can contain additives such as viscosity controlling agent, surface tension controlling agent, specific resistance controlling agent, film-formation controlling agent, UV absorber, antioxidizing agent, anti-fading agent, anti-fungal agent, rust inhibitor, dispersing agent and surface active agent.
  • additives such as viscosity controlling agent, surface tension controlling agent, specific resistance controlling agent, film-formation controlling agent, UV absorber, antioxidizing agent, anti-fading agent, anti-fungal agent, rust inhibitor, dispersing agent and surface active agent.
  • the ink In ink-jet recording, droplets of the aforementioned oily magenta ink (jet printing ink) are ejected to record an image on recording paper (image-receiving material).
  • the ink preferably has a viscosity of not more than 40 cp and a surface tension of 20 to 100 dyn/cm.
  • oily inks of cyan and yellow hues can be used together with the oily magenta ink. Further, an oily ink of black hue can be used to control the tone of the image.
  • the recording paper for ink-jet printing, coat paper is preferred from the viewpoints of quality and durability of the image.
  • Recording paper containing polymer mordant is also preferred.
  • the recording paper may contain an inorganic pigment.
  • the recording paper preferably comprises a hydrophilic ink-receiving layer containing a hydrophilic binder.
  • the binder is preferably hardened with a curing agent.
  • the recording paper may contain a matting agent.
  • the layers constituting the recording paper may contain a surface active agent or an organic fluorine compound, and further may contain a polymer latex, anti-fading agent and a fluorescent whitening dye.
  • Ink-jet recording is usually conducted in an on-demand system or in a continuous system.
  • the head for ink-jet recording i.e., jet head
  • some types such as bubble jet type, thermal jet type and ultrasonic type are known.
  • ink-jet recording method There are also some types of the ink-jet recording method. For example, in one type, many small droplets of thin ink (which is often referred to as “photo-ink”) are jetted out. In another type, two or more inks having the same hue but different concentrations are used to improve image quality. Further, colorless and transparent ink can be also usable.
  • photo-ink thin ink
  • two or more inks having the same hue but different concentrations are used to improve image quality.
  • colorless and transparent ink can be also usable.
  • the obtained solution was dropwise added for 1.5 hour to a solution in which 50.0 g of ammonium persulfate was dissolved in 300 ml of water.
  • the resulting solution was made to react for 1 hour.
  • 1,000 ml of ethyl acetate and 1,000 ml of water were added, the organic phase was collected.
  • the collected liquid was twice washed with 1,500 ml of water, and the solvent was distilled off.
  • 300 ml of acetonitrile was added to precipitate a crystalline product.
  • the product was collected and air-dried, and then recrystallized from 300 ml of methanol.
  • 45 g of the azomethine compound (I a - 12 ) was prepared.
  • the yield was 40%, and the melting point was 118-119° C.
  • N-butylaniline and ethylacrylate were made to react to prepare N-butyl-N-(2-ethoxycarbonylethyl)aniline, which was then nitrosoated and reduced to synthesize 4-amino-N-butyl-N-(2-ethoxycarbonylethyl)aniline.
  • the melting points of the compounds (I a - 1 ) and (I a - 6 ) are lower than room temperature (i.e., they are in the form of oily liquid at room temperature).
  • the melting point of the compound (I a - 13 ) was 132-133° C.
  • the melting point of the compound (I a - 14 ) was 119-120° C.
  • the melting point of the compound (I a - 15 ) was 118-120° C.
  • Each prepared ink was concentrated to measure the solubility, but solid (crystallite) was not deposited. This indicates that the solubility of each compound is more than 30 wt. %.
  • the azomethine compounds (X- 1 ), (X- 2 ), (X- 3 ) and (X- 4 ) correspond to the compounds 1, 6, 16 and 18 in Japanese Patent Provisional Publication No. 4(1992)-178646 (pages 11-13), respectively.
US10/095,448 1999-03-12 2002-03-13 Azomethine compound and oily magenta ink Abandoned US20020128488A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/095,448 US20020128488A1 (en) 1999-03-12 2002-03-13 Azomethine compound and oily magenta ink

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP11-066722 1999-03-12
JP6672299 1999-03-12
US09/515,846 US6383276B1 (en) 1999-03-12 2000-02-29 Azomethine compound and oily magenta ink
US10/095,448 US20020128488A1 (en) 1999-03-12 2002-03-13 Azomethine compound and oily magenta ink

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/515,846 Division US6383276B1 (en) 1999-03-12 2000-02-29 Azomethine compound and oily magenta ink

Publications (1)

Publication Number Publication Date
US20020128488A1 true US20020128488A1 (en) 2002-09-12

Family

ID=13324089

Family Applications (2)

Application Number Title Priority Date Filing Date
US09/515,846 Expired - Fee Related US6383276B1 (en) 1999-03-12 2000-02-29 Azomethine compound and oily magenta ink
US10/095,448 Abandoned US20020128488A1 (en) 1999-03-12 2002-03-13 Azomethine compound and oily magenta ink

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US09/515,846 Expired - Fee Related US6383276B1 (en) 1999-03-12 2000-02-29 Azomethine compound and oily magenta ink

Country Status (2)

Country Link
US (2) US6383276B1 (US20020128488A1-20020912-C00010.png)
EP (1) EP1035172A3 (US20020128488A1-20020912-C00010.png)

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040202658A1 (en) * 2003-04-09 2004-10-14 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to TNF-alpha inhibitor
US20050032130A1 (en) * 2003-07-29 2005-02-10 Genentech, Inc. Neutralizing antibody assay and uses therefor
US20050053602A1 (en) * 2003-08-29 2005-03-10 Genentech, Inc. Therapy of ocular disorders
US20050070689A1 (en) * 2001-08-03 2005-03-31 Genentech, Inc. Taci and br3 polypeptides and uses thereof
US20050081746A1 (en) * 2002-01-25 2005-04-21 Deardurff Larrie A. Inkjet dye design
US20050095243A1 (en) * 2003-06-05 2005-05-05 Genentech, Inc. Combination therapy for B cell disorders
US20050163775A1 (en) * 2003-06-05 2005-07-28 Genentech, Inc. Combination therapy for B cell disorders
US20050186206A1 (en) * 2003-12-19 2005-08-25 Genentech, Inc. Detection of CD20 in therapy of autoimmune diseases
US20050191297A1 (en) * 2003-12-19 2005-09-01 Genentech, Inc. Detection of CD20 in transplant rejection
US20050271658A1 (en) * 2004-05-05 2005-12-08 Genentech, Inc. Preventing autoimmune disease
US20060024295A1 (en) * 2004-06-04 2006-02-02 Genentech, Inc. Method for treating lupus
US20060034835A1 (en) * 2002-12-16 2006-02-16 Genentech, Inc. Immunoglobulin variants and uses thereof
US20060051345A1 (en) * 2004-06-04 2006-03-09 Genentech, Inc. Method for treating multiple sclerosis
US20060062787A1 (en) * 2004-07-22 2006-03-23 Genentech, Inc. Method for treating Sjogren's syndrome
US20060073146A1 (en) * 2000-02-16 2006-04-06 Genentech, Inc. Uses of agonists and antagonists to modulate activity of TNF-related molecules
US20060110387A1 (en) * 2004-10-05 2006-05-25 Genentech, Inc. Method for treating vasculitis
US20060188495A1 (en) * 2005-01-13 2006-08-24 Genentech, Inc. Treatment method
US20060233797A1 (en) * 2005-04-15 2006-10-19 Genentech, Inc. Treatment of inflammatory bowel disease (IBD)
US20060246004A1 (en) * 2005-02-07 2006-11-02 Genentech, Inc. Antibody variants and uses thereof
US20060263349A1 (en) * 2005-05-20 2006-11-23 Genentech, Inc. Pretreatment of a biological sample from an autoimmune disease subject
US20060263355A1 (en) * 2005-02-28 2006-11-23 Joanne Quan Treatment of bone disorders
US20070212733A1 (en) * 2005-11-23 2007-09-13 Genentech, Inc. Methods and compositions related to B cell assays
US20080075719A1 (en) * 2004-04-16 2008-03-27 Genentech, Inc. Method for Augmenting B Cell Depletion
US20080171036A1 (en) * 2002-07-25 2008-07-17 Anan Chuntharapai Taci antibodies and uses thereof
US20080279850A1 (en) * 2005-07-25 2008-11-13 Trubion Pharmaceuticals, Inc. B-Cell Reduction Using CD37-Specific and CD20-Specific Binding Molecules
EP2077281A1 (en) 2008-01-02 2009-07-08 Bergen Teknologioverforing AS Anti-CD20 antibodies or fragments thereof for the treatment of chronic fatigue syndrome
US20100003252A1 (en) * 1999-07-12 2010-01-07 Genentech, Inc. Blocking immune response to a graft
US20100135900A1 (en) * 2008-11-13 2010-06-03 Trubion Pharmaceuticals, Inc. Cd37 immunotherapeutic combination therapies and uses thereof
EP2233149A1 (en) 2007-10-16 2010-09-29 ZymoGenetics, Inc. Combination of BLYS inhibition and anti-CD20 agents for treatment of autoimmune disease
US7820161B1 (en) 1999-05-07 2010-10-26 Biogen Idec, Inc. Treatment of autoimmune diseases
WO2011019619A1 (en) 2009-08-11 2011-02-17 Genentech, Inc. Production of proteins in glutamine-free cell culture media
EP2295080A2 (en) 2005-07-25 2011-03-16 Trubion Pharmaceuticals, Inc. B-cell reduction using CD37-specific and CD20-specific binding molecules
US7914785B2 (en) 2008-01-02 2011-03-29 Bergen Teknologieverforing As B-cell depleting agents, like anti-CD20 antibodies or fragments thereof for the treatment of chronic fatigue syndrome
US20110142836A1 (en) * 2009-01-02 2011-06-16 Olav Mella B-cell depleting agents for the treatment of chronic fatigue syndrome
EP2415483A1 (en) 2005-07-25 2012-02-08 Emergent Product Development Seattle, LLC Single dose use of cd20-specific binding molecules
US8333966B2 (en) 2008-04-11 2012-12-18 Emergent Product Development Seattle, Llc CD37 immunotherapeutics and uses thereof
US8409577B2 (en) 2006-06-12 2013-04-02 Emergent Product Development Seattle, Llc Single chain multivalent binding proteins with effector function
EP2586788A1 (en) 2007-07-09 2013-05-01 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
US8853366B2 (en) 2001-01-17 2014-10-07 Emergent Product Development Seattle, Llc Binding domain-immunoglobulin fusion proteins
US9005612B2 (en) 2001-01-17 2015-04-14 Emergent Product Development Seattle, Llc Binding domain-immunoglobulin fusion proteins
WO2017055542A1 (en) 2015-10-02 2017-04-06 F. Hoffmann-La Roche Ag Bispecific anti-human cd20/human transferrin receptor antibodies and methods of use
US9683047B2 (en) 2008-09-16 2017-06-20 Genentech, Inc. Methods for treating progressive multiple sclerosis
US10450379B2 (en) 2005-11-15 2019-10-22 Genetech, Inc. Method for treating joint damage
US10941205B2 (en) 2015-10-02 2021-03-09 Hoffmann-La Roche Inc. Bispecific anti-human A-beta/human transferrin receptor antibodies and methods of use
US11352426B2 (en) 2015-09-21 2022-06-07 Aptevo Research And Development Llc CD3 binding polypeptides
US11584793B2 (en) 2015-06-24 2023-02-21 Hoffmann-La Roche Inc. Anti-transferrin receptor antibodies with tailored affinity

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4082848B2 (ja) * 2000-03-21 2008-04-30 富士フイルム株式会社 着色微粒子分散物、インクジェット用インクおよびインクジェット記録方法
JP2001262018A (ja) * 2000-03-21 2001-09-26 Fuji Photo Film Co Ltd インクジェット用インク及びその製造方法、並びに、インクジェット記録方法
JP2001271002A (ja) * 2000-03-27 2001-10-02 Fuji Photo Film Co Ltd 着色組成物、インクジェット用インク及びインクジェット記録方法
JP2001342376A (ja) * 2000-03-29 2001-12-14 Fuji Photo Film Co Ltd 着色組成物、インクジェット用インク及びインクジェット記録方法
JP2001342373A (ja) * 2000-03-30 2001-12-14 Fuji Photo Film Co Ltd 着色組成物、インクジェット用インク、インクジェット記録方法及びインクジェット記録画像のオゾンガス褪色改良方法
JP4077600B2 (ja) * 2000-05-23 2008-04-16 富士フイルム株式会社 インクジェット用インク及びインクジェット記録方法
US6604819B2 (en) 2000-09-28 2003-08-12 Fuji Photo Film Co., Ltd. Ink jet image recording method
JP2002121440A (ja) 2000-10-16 2002-04-23 Fuji Photo Film Co Ltd インクジェット画像記録方法
US7297454B2 (en) * 2002-07-30 2007-11-20 Hewlett-Packard Development Company, L.P. Colorless inkjet ink compositions for improved image quality

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0764993B2 (ja) * 1986-12-09 1995-07-12 富士写真フイルム株式会社 ピラゾロアゾールアゾメチンシアン染料
JPH03231975A (ja) * 1990-02-06 1991-10-15 Fuji Photo Film Co Ltd インクジエツト記録方法
JP2684436B2 (ja) * 1990-02-23 1997-12-03 富士写真フイルム株式会社 熱転写色素供与材料
JP2747848B2 (ja) * 1990-08-03 1998-05-06 富士写真フイルム株式会社 熱転写色素供与材料
JP2964422B2 (ja) * 1990-11-14 1999-10-18 富士写真フイルム株式会社 ピラゾロアゾールアゾメチン色素
JP2665642B2 (ja) * 1992-03-16 1997-10-22 富士写真フイルム株式会社 ピラゾロアゾールアゾメチン色素およびそれを含有する熱転写色素供与材料
US5476943A (en) * 1993-03-22 1995-12-19 Konica Corporation Dye and heat sensitive transfer material comprising the same
JPH10264517A (ja) * 1996-12-09 1998-10-06 Konica Corp 感熱記録材料

Cited By (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9993550B2 (en) 1999-05-07 2018-06-12 Genentech, Inc. Treatment of pemphigus
US7820161B1 (en) 1999-05-07 2010-10-26 Biogen Idec, Inc. Treatment of autoimmune diseases
US8545843B2 (en) 1999-05-07 2013-10-01 Genentech, Inc. Treatment of vasculitis
US20100003252A1 (en) * 1999-07-12 2010-01-07 Genentech, Inc. Blocking immune response to a graft
US20060073146A1 (en) * 2000-02-16 2006-04-06 Genentech, Inc. Uses of agonists and antagonists to modulate activity of TNF-related molecules
US8853366B2 (en) 2001-01-17 2014-10-07 Emergent Product Development Seattle, Llc Binding domain-immunoglobulin fusion proteins
US9005612B2 (en) 2001-01-17 2015-04-14 Emergent Product Development Seattle, Llc Binding domain-immunoglobulin fusion proteins
US20050070689A1 (en) * 2001-08-03 2005-03-31 Genentech, Inc. Taci and br3 polypeptides and uses thereof
US20050081746A1 (en) * 2002-01-25 2005-04-21 Deardurff Larrie A. Inkjet dye design
US7407541B2 (en) * 2002-01-25 2008-08-05 Hewlett-Packard Development Company, L.P. Inkjet dye design
US8119777B2 (en) 2002-01-25 2012-02-21 Hewlett-Packard Development Company, L.P. Ink jet dye design
US7449057B2 (en) 2002-01-25 2008-11-11 Hewlett-Packard Development Company, L.P. Ink jet dye design
US20080078303A1 (en) * 2002-01-25 2008-04-03 Deardurff Larrie A Ink jet dye design
US20080171036A1 (en) * 2002-07-25 2008-07-17 Anan Chuntharapai Taci antibodies and uses thereof
US20060034835A1 (en) * 2002-12-16 2006-02-16 Genentech, Inc. Immunoglobulin variants and uses thereof
US7799900B2 (en) 2002-12-16 2010-09-21 Genentech, Inc. Immunoglobulin variants and uses thereof
US20090155257A1 (en) * 2002-12-16 2009-06-18 Genentech, Inc. Immunoglobulin variants and uses thereof
US8562992B2 (en) 2002-12-16 2013-10-22 Genentech, Inc. Immunoglobulin variants and uses thereof
US20040202658A1 (en) * 2003-04-09 2004-10-14 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to TNF-alpha inhibitor
US7708994B2 (en) 2003-04-09 2010-05-04 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a TNF-α inhibitor
US20060240008A1 (en) * 2003-04-09 2006-10-26 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a TNF-alpha inhibitor
EP2062916A2 (en) 2003-04-09 2009-05-27 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a TNF-Alpha inhibitor
US7976838B2 (en) 2003-04-09 2011-07-12 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a TNF-α inhibitor
US20080213280A1 (en) * 2003-04-09 2008-09-04 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a tnf-alpha inhibitor
WO2004091657A2 (en) 2003-04-09 2004-10-28 Genentech, Inc. Therapy of autoimmune disease in a patient with an inadequate response to a tnf-alpha inhibitor
US20100143352A1 (en) * 2003-06-05 2010-06-10 Genentech, Inc. Combination therapy for b cell disorders
US20050163775A1 (en) * 2003-06-05 2005-07-28 Genentech, Inc. Combination therapy for B cell disorders
US20050095243A1 (en) * 2003-06-05 2005-05-05 Genentech, Inc. Combination therapy for B cell disorders
EP2272868A2 (en) 2003-06-05 2011-01-12 Genentech, Inc. Combination therapy for B cell disorders
US20050032130A1 (en) * 2003-07-29 2005-02-10 Genentech, Inc. Neutralizing antibody assay and uses therefor
US20090136492A1 (en) * 2003-08-29 2009-05-28 Genentech, Inc. Therapy of ocular disorders
US20050053602A1 (en) * 2003-08-29 2005-03-10 Genentech, Inc. Therapy of ocular disorders
US20050186206A1 (en) * 2003-12-19 2005-08-25 Genentech, Inc. Detection of CD20 in therapy of autoimmune diseases
US20050191297A1 (en) * 2003-12-19 2005-09-01 Genentech, Inc. Detection of CD20 in transplant rejection
US20080075719A1 (en) * 2004-04-16 2008-03-27 Genentech, Inc. Method for Augmenting B Cell Depletion
US20050271658A1 (en) * 2004-05-05 2005-12-08 Genentech, Inc. Preventing autoimmune disease
US20060024295A1 (en) * 2004-06-04 2006-02-02 Genentech, Inc. Method for treating lupus
EP3130349A1 (en) 2004-06-04 2017-02-15 Genentech, Inc. Method for treating multiple sclerosis
US20100303810A1 (en) * 2004-06-04 2010-12-02 Genentech, Inc. Method for treating lupus
US20060051345A1 (en) * 2004-06-04 2006-03-09 Genentech, Inc. Method for treating multiple sclerosis
US20100233121A1 (en) * 2004-06-04 2010-09-16 Genentech, Inc. Method for treating multiple sclerosis
US20060062787A1 (en) * 2004-07-22 2006-03-23 Genentech, Inc. Method for treating Sjogren's syndrome
US20070025987A1 (en) * 2004-10-05 2007-02-01 Genentech, Inc. Method for Treating Vasculitis
US20060110387A1 (en) * 2004-10-05 2006-05-25 Genentech, Inc. Method for treating vasculitis
US20080095771A1 (en) * 2005-01-13 2008-04-24 Genentech, Inc. Treatment Method
US20080299117A1 (en) * 2005-01-13 2008-12-04 Barron Hal V Treatment Method
US20060188495A1 (en) * 2005-01-13 2006-08-24 Genentech, Inc. Treatment method
US20060246004A1 (en) * 2005-02-07 2006-11-02 Genentech, Inc. Antibody variants and uses thereof
US20060263355A1 (en) * 2005-02-28 2006-11-23 Joanne Quan Treatment of bone disorders
US20060233797A1 (en) * 2005-04-15 2006-10-19 Genentech, Inc. Treatment of inflammatory bowel disease (IBD)
US7601335B2 (en) 2005-05-20 2009-10-13 Genentech, Inc. Pretreatment of a biological sample from an autoimmune disease subject
US20100015055A1 (en) * 2005-05-20 2010-01-21 Genentech, Inc. Pretreatment of a biological sample from an autoimmune disease subject
US20060263349A1 (en) * 2005-05-20 2006-11-23 Genentech, Inc. Pretreatment of a biological sample from an autoimmune disease subject
US10307481B2 (en) 2005-07-25 2019-06-04 Aptevo Research And Development Llc CD37 immunotherapeutics and uses thereof
EP2298815A1 (en) 2005-07-25 2011-03-23 Trubion Pharmaceuticals, Inc. B-cell reduction using CD37-specific and CD20-specific binding molecules
US20080279850A1 (en) * 2005-07-25 2008-11-13 Trubion Pharmaceuticals, Inc. B-Cell Reduction Using CD37-Specific and CD20-Specific Binding Molecules
US10143748B2 (en) 2005-07-25 2018-12-04 Aptevo Research And Development Llc B-cell reduction using CD37-specific and CD20-specific binding molecules
EP2415483A1 (en) 2005-07-25 2012-02-08 Emergent Product Development Seattle, LLC Single dose use of cd20-specific binding molecules
EP2295080A2 (en) 2005-07-25 2011-03-16 Trubion Pharmaceuticals, Inc. B-cell reduction using CD37-specific and CD20-specific binding molecules
EP2586798A2 (en) 2005-07-25 2013-05-01 Emergent Product Development Seattle, LLC B-cell reduction using CD37-specific and CD20-specific binding molecules
US10654940B2 (en) 2005-11-15 2020-05-19 Genentech, Inc. Method for treating joint damage
US10450379B2 (en) 2005-11-15 2019-10-22 Genetech, Inc. Method for treating joint damage
US9726673B2 (en) 2005-11-23 2017-08-08 Genentech, Inc. Methods and compositions related to B cell assays
US20070212733A1 (en) * 2005-11-23 2007-09-13 Genentech, Inc. Methods and compositions related to B cell assays
US8409577B2 (en) 2006-06-12 2013-04-02 Emergent Product Development Seattle, Llc Single chain multivalent binding proteins with effector function
EP3327026A1 (en) 2007-07-09 2018-05-30 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP2586788A1 (en) 2007-07-09 2013-05-01 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP3597659A1 (en) 2007-07-09 2020-01-22 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP4335863A2 (en) 2007-07-09 2024-03-13 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP4219522A2 (en) 2007-07-09 2023-08-02 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP4245766A2 (en) 2007-07-09 2023-09-20 Genentech, Inc. Prevention of disulfide bond reduction during recombinant production of polypeptides
EP2233149A1 (en) 2007-10-16 2010-09-29 ZymoGenetics, Inc. Combination of BLYS inhibition and anti-CD20 agents for treatment of autoimmune disease
US7914785B2 (en) 2008-01-02 2011-03-29 Bergen Teknologieverforing As B-cell depleting agents, like anti-CD20 antibodies or fragments thereof for the treatment of chronic fatigue syndrome
EP2077281A1 (en) 2008-01-02 2009-07-08 Bergen Teknologioverforing AS Anti-CD20 antibodies or fragments thereof for the treatment of chronic fatigue syndrome
US8333966B2 (en) 2008-04-11 2012-12-18 Emergent Product Development Seattle, Llc CD37 immunotherapeutics and uses thereof
US9101609B2 (en) 2008-04-11 2015-08-11 Emergent Product Development Seattle, Llc CD37 immunotherapeutic and combination with bifunctional chemotherapeutic thereof
US9994642B2 (en) 2008-09-16 2018-06-12 Genentech, Inc. Methods for treating progressive multiple sclerosis
US9683047B2 (en) 2008-09-16 2017-06-20 Genentech, Inc. Methods for treating progressive multiple sclerosis
US20100135900A1 (en) * 2008-11-13 2010-06-03 Trubion Pharmaceuticals, Inc. Cd37 immunotherapeutic combination therapies and uses thereof
US20110142836A1 (en) * 2009-01-02 2011-06-16 Olav Mella B-cell depleting agents for the treatment of chronic fatigue syndrome
US9714293B2 (en) 2009-08-11 2017-07-25 Genentech, Inc. Production of proteins in glutamine-free cell culture media
EP3760712A1 (en) 2009-08-11 2021-01-06 F. Hoffmann-La Roche AG Production of proteins in glutamine-free cell culture media
US10982003B2 (en) 2009-08-11 2021-04-20 Genentech, Inc. Production of proteins in glutamine-free cell culture media
WO2011019619A1 (en) 2009-08-11 2011-02-17 Genentech, Inc. Production of proteins in glutamine-free cell culture media
US8512983B2 (en) 2009-08-11 2013-08-20 Martin Gawlitzek Production of proteins in glutamine-free cell culture media
US11584793B2 (en) 2015-06-24 2023-02-21 Hoffmann-La Roche Inc. Anti-transferrin receptor antibodies with tailored affinity
US11352426B2 (en) 2015-09-21 2022-06-07 Aptevo Research And Development Llc CD3 binding polypeptides
US10941205B2 (en) 2015-10-02 2021-03-09 Hoffmann-La Roche Inc. Bispecific anti-human A-beta/human transferrin receptor antibodies and methods of use
US11603411B2 (en) 2015-10-02 2023-03-14 Hoffmann-La Roche Inc. Bispecific anti-human CD20/human transferrin receptor antibodies and methods of use
WO2017055542A1 (en) 2015-10-02 2017-04-06 F. Hoffmann-La Roche Ag Bispecific anti-human cd20/human transferrin receptor antibodies and methods of use

Also Published As

Publication number Publication date
EP1035172A2 (en) 2000-09-13
US6383276B1 (en) 2002-05-07
EP1035172A3 (en) 2002-11-27

Similar Documents

Publication Publication Date Title
US20020128488A1 (en) Azomethine compound and oily magenta ink
US5753017A (en) Ink jet recording ink and recording method employing the same
JP4731923B2 (ja) 新規な色素化合物、インク、インクタンク、記録ユニット、記録装置及び記録方法
US7504488B2 (en) Dye, dye production method and ink containing dye
JP2001115066A (ja) インクジェット用インク及びインクジェット記録方法
KR20080063771A (ko) 잉크 조성물, 잉크의 제조방법, 잉크세트 및 기록방법
JP3997651B2 (ja) 新規色素及び画像記録材料及び感熱転写材料及びインクジェット記録液
US5413630A (en) Colorant and ink compositions
US6464767B1 (en) Ink jet printing method
US4929277A (en) Recording liquid
US6136080A (en) Cationic azo dye for ink jet ink
JP2002327132A (ja) フタロシアニン染料を含むインクジェット記録用インク及びインクジェット記録方法
EP1364998B1 (en) Ink jet recording liquid
EP1367104B1 (en) Ink jet recording liquid
JP2003268281A (ja) インクジェットインクの組
JP3675025B2 (ja) アゾメチン系化合物及び該化合物を含有するインクジェット記録液
JP2007177254A (ja) 改良された安定性及び耐光堅牢性を有する染料ベースのインクジェット用インク組成物
US6419354B1 (en) Ink jet printer method
JP2000327940A (ja) アゾメチン化合物および油性マゼンタインク
JP2002192828A (ja) インクジェット印刷方法
JP2007070573A (ja) インクセット及びインクジェット記録方法
JPH0688462B2 (ja) 感熱転写記録用色素
GB2396357A (en) Copper phthalocyanine sulphonamide dyestuffs with carboxy & sulpho substituted N-substituent for use in ink jet inks
JP2002114933A (ja) インクジェットインク組成物
JP2006016565A (ja) 色素、金属キレート色素、インクジェット記録用インク、カラートナー及びカラーフィルター

Legal Events

Date Code Title Description
STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION