WO2000059620A1 - Tensioactif ameliore et compositions d'encre pour impression a jet d'encre renfermant ce tensioactif - Google Patents

Tensioactif ameliore et compositions d'encre pour impression a jet d'encre renfermant ce tensioactif Download PDF

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Publication number
WO2000059620A1
WO2000059620A1 PCT/US2000/009224 US0009224W WO0059620A1 WO 2000059620 A1 WO2000059620 A1 WO 2000059620A1 US 0009224 W US0009224 W US 0009224W WO 0059620 A1 WO0059620 A1 WO 0059620A1
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WO
WIPO (PCT)
Prior art keywords
composition
surfactant
carbon atoms
ink jet
alkylaryl group
Prior art date
Application number
PCT/US2000/009224
Other languages
English (en)
Inventor
Ronald Sinclair Nohr
John Gavin Mcdonald
Original Assignee
Kimberly-Clark Worldwide, Inc.
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 Kimberly-Clark Worldwide, Inc. filed Critical Kimberly-Clark Worldwide, Inc.
Priority to AU42085/00A priority Critical patent/AU4208500A/en
Publication of WO2000059620A1 publication Critical patent/WO2000059620A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • 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
    • 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
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Definitions

  • the present invention relates to a new surfactant for colorant compositions, particularly ink jet ink compositions.
  • surfactants include, but are not limited to, surfactants such as cetyl trimethyl arnrnonium chloride, carboxymethylamylose, and ethoxylated acetylene glycols.
  • surfactants such as cetyl trimethyl arnrnonium chloride, carboxymethylamylose, and ethoxylated acetylene glycols.
  • U.S. Patents Nos. 5,601,639 and 5,560,771 disclosed ink jet ink compositions containing one or more surfactants in the form of acetylene glycols.
  • Other ink compositions containing surfactants are disclosed in numerous patents including, but not limited to, U.S. Patents Nos. 4,162,186; 4,210,566; 4,225,475; 4,409,039; 4,954,556; 5,019,166; 5,540,765;
  • the above-mentioned surfactants provide a reduction in the surface tension of a composition. While the above- described surfactants are suitable for a number of ink compositions, the surfactants do not significantly contribute to other desirable properties of the compositions, such as lightfastness.
  • a surfactant which provides the above-mentioned usual surfactant properties, as well as, absorbs UV light and provides an O, barrier, thus protecting a dye molecule associated with the surfactant.
  • an ink composition containing a surfactant wherein the surfactant provides light stability to a colorant within the ink composition.
  • compositions containing a colorant and at least one water-soluble compound having the following general formula:
  • R ⁇ / R 2 , and R 3 each independently comprise -H, -OH, a halogenated alkyl group having from one to six carbon atoms, or an alkylaryl group, wherein the alkyl portion of the moiety has one to six carbon atoms; and x, y, and z each independently comprise an integer from 0 to 12, wherein the sum of x, y, and z is at least one.
  • R ⁇ and R 2 may form a six-member aromatic ring, which may or may not be substituted with one or more "R" groups as described above.
  • the water-soluble compound acts as a surfactant.
  • the compound provides light stability to a colorant associated with the surfactant.
  • the composition comprises an ink jet ink composition. Other compatible components may be added to the mixture to produce a composition having desired properties, such as lightfastness, waterfastness, etc.
  • the present invention is also directed to ink-receiving substrates having the above-described composition thereon.
  • Suitable ink-receiving substrates include substrates such as paper, wood, fabrics and films.
  • the present invention is further directed to a method of prmting an ink composition onto an ink-receiving substrate.
  • the present invention is also directed to a method of making a composition comprising a colorant and at least one water-soluble compound as described above. At least one water-soluble compound is incorporated into a mixture containing a colorant.
  • the present invention is also directed to an ink jet ink cartridge contauiing the above- described composition.
  • compositions of the present invention contain a colorant and at least one water-soluble compound having the following general formula:
  • R lr R 2 , and R 3 each independently comprise -H, -OH, a halogenated alkyl group having from one to six carbon atoms, or an alkylaryl group, wherein the alkyl portion of the moiety has one to six carbon atoms; and x, y, and z each independently comprise an integer from 0 to 12, wherein the sum of x, y, and z is at least one.
  • the compositions possess improved lightfastness when compared to colorant compositions containing known surfactants of the prior art.
  • the present invention is also directed to ink-receiving substrates having the above- described composition thereon.
  • composition and such variations as “colored composition” are used herein to mean a colorant and one or more water-soluble compounds described above.
  • the composition may optionally include other compatible components.
  • colorant is meant to include, without limitation, any material which typically will be an organic material, such as an organic colorant or dye.
  • the term is meant to include a single material or a mixture of two or more materials.
  • surfactant is meant to include, without limitation, any material which lowers the surface tension of a liquid to which the material is added or weakens the interface tension between two adjoining liquids.
  • the term is meant to include a single material or a mixture of two or more materials.
  • the term "thereon” is used herein to mean thereon or therein.
  • the present invention includes a substrate having a colored composition thereon.
  • the colored composition may be present on the substrate or it may be in the substrate.
  • the water-soluble compounds used in the compositions of the present invention have the following general formula:
  • R lr R 2 , and R 3 each independently comprise -H
  • x, y, and z each independently comprise an integer from 0 to 12, wherein the sum of x, y, and z is at least one.
  • x, y, and z each independently comprise an integer from 0 to 6, wherein the sum of x, y, and z is at least four.
  • the substituents R , R 2 , and R 3 are selected to result in a compound, which absorbs ultraviolet light, thereby stabilizing colorants that may be associated with the compound.
  • R x is hydrogen or a hydroxyl group
  • R 2 is a halogenated alkyl group having from one to six carbon atoms
  • R 3 is a halogenated alkyl group having from one to six carbon atoms.
  • ⁇ is a hydroxyl group
  • R 2 is -CF 3
  • R 3 is -CF 3 .
  • the water-soluble compound comprises
  • R l R 2 , and R 3 comprise substituents as described above, and z comprises an integer from 0 to 6.
  • the water-soluble compound comprises
  • R ⁇ and R 2 form a six-member aromatic ring, which may or may not be substituted with one or more "R" groups as described above.
  • the water-soluble compound has the following formula:
  • R 4 , R 5 , R 6 , and R 7 each independently comprise -H, -OH, a halogenated alkyl group having from one to six carbon atoms, or an alkylaryl group, wherein the alkyl portion of the moiety has one to six carbon atoms.
  • the water-soluble compound comprises
  • the water- soluble compound comprises
  • x, y, and z comprise integers as described above.
  • the surfactant may be present in the composition in any amount as long as the composition is suitable for use.
  • the amount of surfactant may need to be less than for another type of coating.
  • the amount of surfactant in the composition of the present invention is up to about 5 weight percent based on the total weight of the composition.
  • the surfactant is present in an amount of about 0.1 to about 2.5 weight percent based on the total weight of the composition.
  • the surfactant is present in an amount of about 0.1 to about 1.0 weight percent based on the total weight of the composition.
  • compositions of the present invention may include any colorant known in the art. Suitable colorants include, bur are not limited to, dyes and pigments. Desirably, the colorant is an organic dye.
  • Organic dye classes include, by way of illustration only, triarylmethyl dyes, such as Malachite Green Carbinol base ⁇ 4-(dirnethylamino)-a-[4- (dimemylarnino)phenyl]-a-phenyl-benzene-methanol ⁇ , Malachite Green Carbinol hydrochloride ⁇ N-4-[[4- (djjnemylamino)phenyl]phenyl- ⁇ ethylene]-2,5- cyclohexyldien-l-yhdene]-N-n emyl-memanan ⁇ inium chloride or bis[p-(dirnemylamino)phenyl]phenyj ⁇ nemylium chloride ⁇ , and Malachite Green oxalate ⁇ N-4-[[4
  • fluorescein dyes such as Huorescemarnine (5- arninofluorescein); diazonium salt dyes, such as Diazo Red RC (Azoic Diazo No. 10 or Fast Red RC salt; 2-methoxy-5- chlorobenzenediazonium chloride, zinc chloride double salt); azoic diazo dyes, such as Fast Blue BB salt (Azoic Diazo No.
  • phenylenediamine dyes such as Disperse Yellow 9 [N-(2,4-dinitrophenyl)-l,4- phenylenediamine or Solvent Orange 53]; diazo dyes, such as Disperse Orange 13 [Solvent Orange 52; l-phenylazo-4- (4-hydroxyphenylazo)naphthalene]; anthra-quinone dyes, such as Disperse Blue 3 [Celliton Fast Blue FFR; 1- methylamino-4-(2-hydroxyethylarnino)-9,10-antlu , aquinone], Disperse Blue 14 [Celliton Fast Blue B; l,4-bis(memylarnino)-
  • trisazo dyes such as Direct Blue 71 ⁇ Benzo Light Blue FFL or Sirius Light Blue BRR; 3-[(4-[(4-[(6-amino-l- hy droxy-3-sulf o-2-naphthalenyl) azo] -6-sulf o-l - naphthalenyl)-azo]-l-naphthalenyl)azo]-l,5- naphthalenedisulfonic acid tetrasodium salt ⁇ ; xanthene dyes, such as 2,7-dichloro-fluorescein; proflavine dyes, such as 3,6-diaminoacridine hemisulfate (Proflavine); sulfonaphthalein dyes, such as Cresol Red (o- cresolsulfonaphthalein); phthalocyanine dyes, such as
  • carotenoid dyes such as trans- ⁇ -carotene (Food Orange 5); caiTninic acid dyes, such as Carmine, the aluminum or caldurn-aluminum lake of carrninic acid (7-a-D- glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-l-methyl- 9,10-dioxo-2-anthracene-carbonylic acid); azure dyes, such as Azure A [3-amino-7-(dj nemylammo)phenot azin-5-ium chloride or hydrochloride]; and acridine dyes, such as Acridine Orange
  • the colorant compositions of the present invention may contain a number of additional components depending on the desired properties of the resulting composition.
  • one or more colorant stabilizers may be added to the composition.
  • a colorant stabilizer in the form of a porphine is added to the colorant composition.
  • Suitable porphines include, but are not limited to, porphines such as those disclosed in U.S. Patent No. 5,782,963 and U.S. Patent Applications Serial Nos. 08/788,863 and 08/843,410, all of which are assigned to Kimberly Clark
  • the colored compositions of the present invention may contain additional components, depending upon the application for which it is intended.
  • additional components include, but are not limited to, buffering agents; charge carriers; stabilizers against thermal oxidation; viscoelastic properties modifiers; cross-linking agents; plasticizers; charge control additives such as a quaternary ammonium salt; flow control additives such as hydrophobic silica, zinc stearate, calcium stearate, lithium stearate, polyvinylstearate, and polyethylene powders; fillers such as calcium carbonate, clay and talc; other surfactants; chelating agents; and TINUVIN® compounds; among other additives used by those having ordinary skill in the art.
  • TINUVIN® compounds are a class of compounds produced by Ciba-Geigy Corporation, which includes benzophenones, benzotriazoles and hindered amines. Desirable TINUVIN® compounds include, but are not limited to, 2-(2'-hydroxy-3'-sec-butyl-5'-fert-butylphenyl)- benzo-triazole, poly-(N- ⁇ -hydroxyethyl-2,2,6,6-tetramethyl- 4-hydroxy-piperidyl succinate and 2-(2'-hydroxy-3',5'- ditertbutylphenyl)-5-chloro-benzotriazole. The identities and amounts of such additional components in the colored composition are well known to one of ordinary skill in the art.
  • Suitable solvents include, but are not limited to, amides, such as N,N-dimethylf ormamide; sulf oxides, such as dimethylsulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl butyl ketone; aliphatic and aromatic hydrocarbons, such as hexane, octane, benzene, toluene, and the xylenes; esters, such as ethyl acetate; water; and the like. Desirably, the solvent is water.
  • amides such as N,N-dimethylf ormamide
  • sulf oxides such as dimethylsulfoxide
  • ketones such as acetone, methyl ethyl ketone, and methyl butyl ketone
  • aliphatic and aromatic hydrocarbons such as hexane, octane, benzene, toluene, and the x
  • the present invention is also directed to ink-receiving substrates having the above-described composition thereon.
  • the substrates to which the colorant and water-soluble compounds are applied include, but are not limited to, paper, wood, a wood product or composite, woven fabric, nonwoven fabric, textile, plastic, glass, metal, or any other substrate that would benefit from having a colorant thereon. Examples of suitable substrates are disclosed in U.S. Patent Applications Serial Nos. 08/843,410; 09/058,385; and 09/133,574; all of which are assigned to Kimberly Clark
  • the present invention is also directed to a method of making a composition comprising a colorant and at least one surfactant as described above. At least one surfactant is incorporated into a mixture containing a colorant.
  • the method of combining the colorant and surfactant may be any method known to those of ordinary skill in the art.
  • the present invention is further directed to a method of printing an ink composition onto an ink-receiving substrate.
  • an ink composition comprising a colorant and at least one surfactant is ejected from an ink jet head onto an ink-receiving surface.
  • the present invention is further directed to an ink jet ink cartridge containing the above- described composition.
  • magenta ink A magenta ink was prepared using the following components, given in weight percent:
  • Surfactant A had the following structure:
  • the resulting ink compositions were applied to ink- receiving substrates as in Example 1.
  • the applied ink compositions were found to have superior lightfastness.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

L'invention concerne un tensioactif ayant la structure (I). Dans cette structure, R1, R2, et R3 sont chacun indépendamment -H, -OH, un groupe alkyle halogéné comportant entre un et six atomes de carbone, ou un groupe alkylaryle, la partie alkyle de la fraction comprenant entre un et six atomes de carbone; et x, y, et z sont chacun indépendamment un entier allant de 0 à 12, sachant que (x + y + z ≥ 1). L'invention concerne en outre des compositions renfermant ce tensioactif.
PCT/US2000/009224 1999-04-07 2000-04-07 Tensioactif ameliore et compositions d'encre pour impression a jet d'encre renfermant ce tensioactif WO2000059620A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU42085/00A AU4208500A (en) 1999-04-07 2000-04-07 Improved surfactant and ink jet ink compositions containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12815099P 1999-04-07 1999-04-07
US60/128,150 1999-04-07

Publications (1)

Publication Number Publication Date
WO2000059620A1 true WO2000059620A1 (fr) 2000-10-12

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AU (1) AU4208500A (fr)
WO (1) WO2000059620A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1300244A1 (fr) * 2001-10-05 2003-04-09 Eastman Kodak Company Composition d'encre

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58217569A (ja) * 1982-06-11 1983-12-17 Ricoh Co Ltd インクジェット記録用インク

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58217569A (ja) * 1982-06-11 1983-12-17 Ricoh Co Ltd インクジェット記録用インク

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198405, 17 December 1983 Derwent World Patents Index; Class A, AN 1984-026867, XP002146439 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1300244A1 (fr) * 2001-10-05 2003-04-09 Eastman Kodak Company Composition d'encre
US6585362B2 (en) 2001-10-05 2003-07-01 Eastman Kodak Company Ink composition, ink cartridge having ink composition, and method of filling ink cartridge
US6824260B2 (en) 2001-10-05 2004-11-30 Eastman Kodak Company Ink composition, ink cartridge having ink composition, and method of filling ink cartridge

Also Published As

Publication number Publication date
AU4208500A (en) 2000-10-23

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