US20060000034A1 - Textile ink composition - Google Patents
Textile ink composition Download PDFInfo
- Publication number
- US20060000034A1 US20060000034A1 US10/881,671 US88167104A US2006000034A1 US 20060000034 A1 US20060000034 A1 US 20060000034A1 US 88167104 A US88167104 A US 88167104A US 2006000034 A1 US2006000034 A1 US 2006000034A1
- Authority
- US
- United States
- Prior art keywords
- dye
- metal oxide
- composition
- acid
- cationically charged
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 239000004753 textile Substances 0.000 title claims abstract description 31
- 239000000975 dye Substances 0.000 claims abstract description 69
- 239000004744 fabric Substances 0.000 claims abstract description 45
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 27
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 26
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 22
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 15
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 hydroxyazo Chemical group 0.000 claims abstract description 9
- 238000004043 dyeing Methods 0.000 claims abstract description 8
- DGQLVPJVXFOQEV-NGOCYOHBSA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-NGOCYOHBSA-N 0.000 claims abstract description 6
- 229940114118 carminic acid Drugs 0.000 claims abstract description 6
- 235000012730 carminic acid Nutrition 0.000 claims abstract description 6
- 239000004106 carminic acid Substances 0.000 claims abstract description 6
- LNXMADNIUWFTPP-UHFFFAOYSA-L chembl2028186 Chemical compound [Na+].[Na+].OC1=CC=C(Cl)C=C1N=NC1=C(O)C2=C(O)C=C(S([O-])(=O)=O)C=C2C=C1S([O-])(=O)=O LNXMADNIUWFTPP-UHFFFAOYSA-L 0.000 claims abstract description 6
- BEQIIZJSZSVJJK-UHFFFAOYSA-M chembl2028372 Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1N=NC1=C(O)C=CC2=CC=CC=C12 BEQIIZJSZSVJJK-UHFFFAOYSA-M 0.000 claims abstract description 6
- MVQBFZXBLLMXGS-UHFFFAOYSA-N chembl331220 Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C=C(S(O)(=O)=O)C2=C1 MVQBFZXBLLMXGS-UHFFFAOYSA-N 0.000 claims abstract description 6
- FFUMCSDSJNSMQH-HEXQVDJKSA-K chromoxane cyanin R Chemical compound [Na+].[Na+].[Na+].C1=C(C([O-])=O)C(=O)C(C)=C\C1=C(C=1C(=CC=CC=1)S([O-])(=O)=O)\C1=CC(C)=C(O)C(C([O-])=O)=C1 FFUMCSDSJNSMQH-HEXQVDJKSA-K 0.000 claims abstract description 6
- FBNOWTWLVCWGCZ-UHFFFAOYSA-L disodium 6-[(5-chloro-2-hydroxy-4-sulfonatophenyl)diazenyl]-5-hydroxynaphthalene-1-sulfonate Chemical compound [Na+].[Na+].Oc1cc(c(Cl)cc1N=Nc1ccc2c(cccc2c1O)S([O-])(=O)=O)S([O-])(=O)=O FBNOWTWLVCWGCZ-UHFFFAOYSA-L 0.000 claims abstract description 6
- LERIXBKRKBHLHG-UHFFFAOYSA-L disodium;2-[[5,8-dihydroxy-4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]-5-methylbenzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=C(O)C=CC(O)=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O LERIXBKRKBHLHG-UHFFFAOYSA-L 0.000 claims abstract description 6
- WSALIDVQXCHFEG-UHFFFAOYSA-L disodium;4,8-diamino-1,5-dihydroxy-9,10-dioxoanthracene-2,6-disulfonate Chemical compound [Na+].[Na+].O=C1C2=C(N)C=C(S([O-])(=O)=O)C(O)=C2C(=O)C2=C1C(O)=C(S([O-])(=O)=O)C=C2N WSALIDVQXCHFEG-UHFFFAOYSA-L 0.000 claims abstract description 6
- RFIRVJCZAAJILM-UHFFFAOYSA-M sodium 4-[(4-aminophenyl)diazenyl]-2-carboxyphenolate Chemical compound [Na+].NC1=CC=C(C=C1)N=NC1=CC=C(C(C(=O)[O-])=C1)O RFIRVJCZAAJILM-UHFFFAOYSA-M 0.000 claims abstract description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 5
- LVYZJEPLMYTTGH-UHFFFAOYSA-H dialuminum chloride pentahydroxide dihydrate Chemical group [Cl-].[Al+3].[OH-].[OH-].[Al+3].[OH-].[OH-].[OH-].O.O LVYZJEPLMYTTGH-UHFFFAOYSA-H 0.000 claims abstract description 5
- 239000000983 mordant dye Substances 0.000 claims abstract description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 5
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZHFPEICFUVWJIS-UHFFFAOYSA-M sodium 2-hydroxy-5-[(3-nitrophenyl)diazenyl]benzoate Chemical compound [Na+].Oc1ccc(cc1C([O-])=O)N=Nc1cccc(c1)[N+]([O-])=O ZHFPEICFUVWJIS-UHFFFAOYSA-M 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 12
- 229920000742 Cotton Polymers 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 229940121375 antifungal agent Drugs 0.000 claims description 3
- 239000003429 antifungal agent Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- 230000035515 penetration Effects 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 239000002964 rayon Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 3
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 3
- 239000000976 ink Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- JKYKXTRKURYNGW-UHFFFAOYSA-N 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C(S(O)(=O)=O)=C2 JKYKXTRKURYNGW-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000004758 synthetic textile Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000010412 laundry washing Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/67341—Salts or hydroxides of elements different from the alkaline or alkaline-earth metals or with anions containing those elements
-
- 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
- D06P5/001—Special chemical aspects of printing textile materials
-
- 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
- D06P5/30—Ink jet printing
Definitions
- the present invention relates to textile ink compositions that are capable of durably dyeing two or more types of fabric. A method of preparing such a composition is also disclosed.
- a simple application of a dye solution onto cotton or polyester fabrics usually fails to durably dye the fabric, and the dye is simply washed out upon laundering of the fabric. This is due to the absence of any specific interaction mechanisms or covalent attachment between the fibers and the dye molecules.
- dyes require some form of pre- or post-dye treatment of the fabric in order to durably dye the fabric.
- developed dyes require the fabric to be first treated with a direct dye, then treated with an acid and further treated with a developer solution; naphthol dyes are applied by impregnation of the fabric with a caustic solution of beta-naphthol and the fabric is then immersed in a second dye solution; and vat dyes are applied to fabrics in a reduced, soluble form and are then re-oxidized to their original, insoluble form.
- washfastness is a measure of the resistance of a dye to washing out of the textile fiber. There is not necessarily any relationship between washfastness and lightfastness, which is a measure of how resistant a dye is to fading due to exposure to light.
- Covalent attachment of dyes to a cationic polymer on a laboratory scale is also known, but it is not economically feasible to scale up this reaction for commercial production.
- a printer cartridge containing a textile ink composition for printing on one type of fabric cannot be used for printing on another type of fabric.
- a printer is used in printing a number of types of fabrics, different cartridges for the same color ink are required.
- the textile ink composition includes an irreversible polymeric cationic dye complex formed between a cationically charged metal oxide and a dye.
- the metal oxide may be any cationic metal oxide, but is typically an alumina oligomer, such as oligomeric aluminum chlorohydrate (also known as aluminum chlorohydrol).
- the dye typically contains anthraquinone, catechol, hydroxyazo or salicylic acid groups.
- Such dyes include Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol and Acid Alizarin Violet N.
- the textile ink composition is capable of durably dyeing a number of both natural and synthetic fabrics, such as cotton, silk, linen, rayon, nylon, polyester and so forth.
- the ratio of alumina oligomer:dye molecule is in the range of from about 0.1:10 to 10:1, more particularly from about 0.5:1 to 5:1 and most particularly about one alumina oligomer per dye molecule.
- the textile ink composition may be used for inkjet printing, silk screening, gravure printing, dip and nip methods and the like.
- the composition may further include one or more additives such as known polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, antifungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- additives such as known polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, antifungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- the invention provides textile ink compositions that are capable of durably dyeing more than one type of fabric, and preferably more than two types of fabric.
- the composition may be capable of dyeing both natural and synthetic fabrics, such as cotton, silk, silk charmeuse, linen, nylon, rayon and polyester.
- compositions require no pre- or post-treatment, can be prepared in a single step and are shelf-stable at room temperature without precipitation.
- the textile ink composition is obtained by mixing a cationically charged metal oxide, such as an alumina oligomer or polymer, and a dye, which react to form an irreversible metal oxide-dye complex.
- a cationically charged metal oxide such as an alumina oligomer or polymer
- a dye which react to form an irreversible metal oxide-dye complex.
- a suitable alumina oligomer is aluminum chlorohydrate (also known as aluminum chlorohydrol), which is available from Reheis of Berkeley, N.J.
- Aluminum chlorohydrol is formed from the reaction: 2Al(OH)3+nHCl 2Al 2 (OH) n Cl 6-n +nH 2 O. It is soluble in water and is sold as a 50 weight percent solution.
- Aluminum chlorohydrol has a high cationic charge, is inexpensive and is readily available in large quantities.
- suitable aluminum oxides having particles ranging from nanometer to micrometer in size are also suitable, for example SNOWTEX AK® from Nissan Chemical and LUDOX® from Grace of Columbia, M.D.
- Suitable dyes are those dye containing anthraquinone, catechol, hydroxyazo or salicylic acid groups. Such dyes include Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol and Acid Alizarin Violet N. Mordant dyes known to form highly colored complexes with chromium, such as Mordant Yellow 12 and Mordant Blue 9, can also be used to produce an ink composition according to the invention. The dyes are obtainable from Aldrich Chemical Corporation of Milwaukee, Wis.
- the ratio of metal oxide oligomer:dye molecule is in the range of from about 1:10 to 10:1, more particularly from about 5:1 to 5:1 and most particularly about one metal oxide oligomer per dye molecule.
- the ink compositions were formed by mixing 1 ml of a 1 weight percent dye solution with from 1 to 200, more preferably from 10 to 100, and even more preferably with about 25 microliters of a 50 weight percent alumina oligomer.
- the dye may be a 20 mM solution.
- the composition can be formed at room temperature, optionally with stirring of the mixture for about two to sixty minutes, and typically for about 30 minutes, so as to ensure that the reaction proceeds to completion.
- the composition may further include one or more known additives such as polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, anti-fungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- additives such as polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, anti-fungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- the textile ink composition is suitable for inkjet printing, silk screening, gravure printing, dip and nip methods and so forth.
- Textile ink compositions prepared according to the invention were spotted onto various fabrics, which were then briefly heated so as to bind the dye to the fabric. Alternatively, the fabrics could be ironed for the same period.
- the washfastness of the ink compositions on the fabrics was determined using the American Association of Textile Chemists and Colorists (AATCC) (http://www.aatcc.org/technical/test_methods/topic_list.htm) Washfast Test Method 61-2003, which used detergent (TIDE® from Procter & Gamble, USA) and hot water (about 90 degrees Celsius), and ball bearings for abrasiveness.
- AATCC American Association of Textile Chemists and Colorists
- TIDE® from Procter & Gamble, USA
- hot water about 90 degrees Celsius
- ball bearings for abrasiveness was determined by subjecting the dyed fabrics to a standard domestic laundry washing cycle.
- the washfastness may be determined by any method known to those skilled in the art as
- Color measurements were performed on the fabrics prior to and after washing to determine the amount of fading, if any.
- Color measurement refers to the interpretation of the visual sensation of color in terms of three numbers that can be used to objectively assess and quantify differences in color between objects. Instruments are available that measure the spectrum of light reflected from the surface of an object and translate this spectrum into a series of numbers that pertain to visual color sensations. For instance, the subjective term ‘brightness’ may be quantified using the objective quantity ‘luminance’ obtained using a color measuring instrument.
- L*a*b* color values measurements (CIE 1976 Commission Internationale de I'Eclairage) and optical density were made of the printed textile fabrics using a handheld spectrophotometer, in accordance with the operator's manual.
- the spectrophotometer was manufactured by Minolta Co. Ltd of Osaka, Japan (Model #M2600d). The spectrophotometer was calibrated against a pure white material that had been provided with the spectrophotometer.
- Average optical densities were taken as the sum of the average of three measurements using each filter.
- a series of textile inks was prepared by mixing a cationically charged metal oxide with a number of dyes.
- the cationically charged metal oxide that was used in the example was a 50 weight percent aqueous solution of aluminum chlorohydrol obtained from Reheis.
- the dyes used in the example were Carminic Acid, Alizarin Red S, Acid Blue 45, Acid Green 41, Mordant Yellow 12, Hematoxylin, Mordant Blue 9, Chromoxane Cyanine R, Calcon Carboxylic Acid, Plasmocorinth B, Pyrocatechol, Acid Alizarin Violet N and Alizarin Yellow GG, obtained from Aldrich Chemical Corporation.
- the textile ink compositions were formed by adding 25 microliters of the aluminum chlorohydrol solution to 1 ml of a 20 mM solution of each dye at room temperature, and the mixture was stirred vigorously for 30 minutes.
- Each textile ink composition was then spotted onto separate cotton and polyester textile fabrics by applying a 10-20 microliter drop of the ink composition onto the fabric surface.
- the polyester fabric was then briefly heated at about 180 degrees Celsius for about 2 to 3 minutes in order to bind the dye onto the fiber surface of the fabric.
- Textile ink compositions were prepared as described in example 1 and were spotted onto cotton and polyester fabrics. The fabrics were then washed in a domestic washing machine on the harshest washing cycle, using the recommended dosage of a domestic laundry detergent (TIDE® from Procter & Gamble, USA) and hot water (about 90 degrees Celsius) for up to 30 minutes.
- TIDE® domestic laundry detergent
- the color intensities and washfast values were calculated as described above, and the results that were obtained were similar to those in example 1.
- this is a fairly harsh washfast test for any printed ink, and the results of this test are thus a good indication that the ink compositions are able to durably dye different fabrics.
- Textile ink compositions prepared according to example 1 were spotted onto a silk charmeuse fabric and allowed to dry.
- the washfastness was tested using the AATCC Washfast Test Method 61-2003 described above, and the fabric colors prior to and after the wash test were analyzed qualitatively (results not shown).
- the ink compositions were shown to dye silk fabric equally well.
- the ink compositions of the present invention are able to incorporate more dye than many other inks, are soluble and are therefore readily incorporated into inkjet inks, and do not have lightfast issues that are associated with other inks.
Abstract
A textile ink composition and a method of manufacturing a textile ink composition are disclosed. The textile ink composition is formed from a cationically charged metal oxide and a dye, and is capable of durably dyeing different types of fabric. The cationically charged metal oxide is typically an oligomer, such as an alumina oligomer. A suitable alumina oligomer is aluminum chlorohydrate. Typical dyes have anthraquinone, catechol, hydroxyazo or salicylic acid groups or are mordant dyes, such as Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol, Acid Alizarin Violet N, Alizarin Yellow GG, Mordant Yellow 12 and Mordant Blue 9.
Description
- The present invention relates to textile ink compositions that are capable of durably dyeing two or more types of fabric. A method of preparing such a composition is also disclosed.
- A simple application of a dye solution onto cotton or polyester fabrics usually fails to durably dye the fabric, and the dye is simply washed out upon laundering of the fabric. This is due to the absence of any specific interaction mechanisms or covalent attachment between the fibers and the dye molecules.
- Only a few commercially available dyes can be used to form washfast textile inks in this manner, and these inks are generally specific to only one type of fabric. For example, fiber reactive dyes are able to durably dye cotton, but not polyester.
- Most dyes require some form of pre- or post-dye treatment of the fabric in order to durably dye the fabric. Thus, developed dyes require the fabric to be first treated with a direct dye, then treated with an acid and further treated with a developer solution; naphthol dyes are applied by impregnation of the fabric with a caustic solution of beta-naphthol and the fabric is then immersed in a second dye solution; and vat dyes are applied to fabrics in a reduced, soluble form and are then re-oxidized to their original, insoluble form.
- Cationically charged dyes tend to bind tightly to some negatively charged fiber surfaces to form durable washfast complexes. However, these dyes are generally not lightfast or washfast on polyester textiles. Washfastness is a measure of the resistance of a dye to washing out of the textile fiber. There is not necessarily any relationship between washfastness and lightfastness, which is a measure of how resistant a dye is to fading due to exposure to light.
- Covalent attachment of dyes to a cationic polymer on a laboratory scale is also known, but it is not economically feasible to scale up this reaction for commercial production.
- As there is no universal dye for textiles, a printer cartridge containing a textile ink composition for printing on one type of fabric cannot be used for printing on another type of fabric. Thus, where a printer is used in printing a number of types of fabrics, different cartridges for the same color ink are required.
- There is therefore a need for textile ink compositions that can durably dye two or more types of fabric and that are economically feasible to produce on a commercial scale.
- In response to the discussed difficulties and problems encountered in the prior art, a new textile ink composition that is capable of durably dyeing two or more, and preferably at least three, fabrics has been discovered. The textile ink composition includes an irreversible polymeric cationic dye complex formed between a cationically charged metal oxide and a dye.
- The metal oxide may be any cationic metal oxide, but is typically an alumina oligomer, such as oligomeric aluminum chlorohydrate (also known as aluminum chlorohydrol).
- The dye typically contains anthraquinone, catechol, hydroxyazo or salicylic acid groups. Such dyes include Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol and Acid Alizarin Violet N. Mordant dyes known to form highly colored complexes with chromium, such as Mordant Yellow 12 and Mordant Blue 9, are also suitable dyes.
- The textile ink composition is capable of durably dyeing a number of both natural and synthetic fabrics, such as cotton, silk, linen, rayon, nylon, polyester and so forth.
- In general, the ratio of alumina oligomer:dye molecule is in the range of from about 0.1:10 to 10:1, more particularly from about 0.5:1 to 5:1 and most particularly about one alumina oligomer per dye molecule.
- The textile ink composition may be used for inkjet printing, silk screening, gravure printing, dip and nip methods and the like.
- The composition may further include one or more additives such as known polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, antifungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- The invention provides textile ink compositions that are capable of durably dyeing more than one type of fabric, and preferably more than two types of fabric. The composition may be capable of dyeing both natural and synthetic fabrics, such as cotton, silk, silk charmeuse, linen, nylon, rayon and polyester.
- The compositions require no pre- or post-treatment, can be prepared in a single step and are shelf-stable at room temperature without precipitation.
- The textile ink composition is obtained by mixing a cationically charged metal oxide, such as an alumina oligomer or polymer, and a dye, which react to form an irreversible metal oxide-dye complex.
- A suitable alumina oligomer is aluminum chlorohydrate (also known as aluminum chlorohydrol), which is available from Reheis of Berkeley, N.J. Aluminum chlorohydrol is formed from the reaction: 2Al(OH)3+nHCl 2Al2(OH)nCl6-n+nH2O. It is soluble in water and is sold as a 50 weight percent solution. Aluminum chlorohydrol has a high cationic charge, is inexpensive and is readily available in large quantities.
- Other suitable aluminum oxides having particles ranging from nanometer to micrometer in size are also suitable, for example SNOWTEX AK® from Nissan Chemical and LUDOX® from Grace of Columbia, M.D.
- Suitable dyes are those dye containing anthraquinone, catechol, hydroxyazo or salicylic acid groups. Such dyes include Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol and Acid Alizarin Violet N. Mordant dyes known to form highly colored complexes with chromium, such as Mordant Yellow 12 and Mordant Blue 9, can also be used to produce an ink composition according to the invention. The dyes are obtainable from Aldrich Chemical Corporation of Milwaukee, Wis.
- In general, the ratio of metal oxide oligomer:dye molecule is in the range of from about 1:10 to 10:1, more particularly from about 5:1 to 5:1 and most particularly about one metal oxide oligomer per dye molecule.
- It will be apparent to a skilled person, however, that as the purity of the dye is often not provided, and it is known that impurities in dyes can range from 10 to 70 percent (and sometimes higher), it is difficult to achieve a precise ratio in practice.
- Typically, the ink compositions were formed by mixing 1 ml of a 1 weight percent dye solution with from 1 to 200, more preferably from 10 to 100, and even more preferably with about 25 microliters of a 50 weight percent alumina oligomer. The dye may be a 20 mM solution.
- The composition can be formed at room temperature, optionally with stirring of the mixture for about two to sixty minutes, and typically for about 30 minutes, so as to ensure that the reaction proceeds to completion.
- The composition may further include one or more known additives such as polyols, viscosity modifiers, non-ionic surfactants to reduce surface tension, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, anti-fungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents, chelating agents and the like.
- The textile ink composition is suitable for inkjet printing, silk screening, gravure printing, dip and nip methods and so forth.
- Textile ink compositions prepared according to the invention were spotted onto various fabrics, which were then briefly heated so as to bind the dye to the fabric. Alternatively, the fabrics could be ironed for the same period. The washfastness of the ink compositions on the fabrics was determined using the American Association of Textile Chemists and Colorists (AATCC) (http://www.aatcc.org/technical/test_methods/topic_list.htm) Washfast Test Method 61-2003, which used detergent (TIDE® from Procter & Gamble, USA) and hot water (about 90 degrees Celsius), and ball bearings for abrasiveness. In another test, the washfastness was determined by subjecting the dyed fabrics to a standard domestic laundry washing cycle. The washfastness may be determined by any method known to those skilled in the art as long as the inventive and non-inventive samples are tested in the same manner.
- Color measurements were performed on the fabrics prior to and after washing to determine the amount of fading, if any. Color measurement refers to the interpretation of the visual sensation of color in terms of three numbers that can be used to objectively assess and quantify differences in color between objects. Instruments are available that measure the spectrum of light reflected from the surface of an object and translate this spectrum into a series of numbers that pertain to visual color sensations. For instance, the subjective term ‘brightness’ may be quantified using the objective quantity ‘luminance’ obtained using a color measuring instrument.
- L*a*b* color values measurements (CIE 1976 Commission Internationale de I'Eclairage) and optical density were made of the printed textile fabrics using a handheld spectrophotometer, in accordance with the operator's manual. The spectrophotometer was manufactured by Minolta Co. Ltd of Osaka, Japan (Model #M2600d). The spectrophotometer was calibrated against a pure white material that had been provided with the spectrophotometer.
- Average optical densities were taken as the sum of the average of three measurements using each filter. Delta E (DE or ΔE) is calculated in accordance with the following equation:
DE=SQRT[(L*standard−L*sample)2+(a*standard−a*sample)2+(b*standard−b*sample)2] - The higher the Delta E, the greater the change in color intensity. Unless the color's intensity is increased by a curing step, a large increase in delta E would typically be indicative of fading. The testing was in accordance with ASTM DM 224-93 and ASTM E308-90. Where values for delta E are less than 3.0, it is generally accepted that such color change cannot be observed with the human eye. A detailed description of spectrophotometer testing is available in Color Technology in the Textile Industry, 2nd Edition, (order no. 9713) Published 1997 by AATCC.
- The present invention is further described by the following examples. Such examples, however, are not to be construed as limiting in any way either the spirit or scope of the present invention.
- A series of textile inks was prepared by mixing a cationically charged metal oxide with a number of dyes. The cationically charged metal oxide that was used in the example was a 50 weight percent aqueous solution of aluminum chlorohydrol obtained from Reheis. The dyes used in the example were Carminic Acid, Alizarin Red S, Acid Blue 45, Acid Green 41, Mordant Yellow 12, Hematoxylin, Mordant Blue 9, Chromoxane Cyanine R, Calcon Carboxylic Acid, Plasmocorinth B, Pyrocatechol, Acid Alizarin Violet N and Alizarin Yellow GG, obtained from Aldrich Chemical Corporation.
- The textile ink compositions were formed by adding 25 microliters of the aluminum chlorohydrol solution to 1 ml of a 20 mM solution of each dye at room temperature, and the mixture was stirred vigorously for 30 minutes.
- Each textile ink composition was then spotted onto separate cotton and polyester textile fabrics by applying a 10-20 microliter drop of the ink composition onto the fabric surface. The polyester fabric was then briefly heated at about 180 degrees Celsius for about 2 to 3 minutes in order to bind the dye onto the fiber surface of the fabric.
- The washfastness of the ink compositions on the fabrics was then determined using the AATCC Washfast Test Method 61-2003. The delta E and washfast values are shown in Table 1.
TABLE 1 Color loss values of alumina oligomer-dye ink compositions applied onto cotton and polyester fabrics Dye complexed with aluminum Cotton fabric Polyester fabric chlorohydrol (ΔE) W/F (ΔE) W/F Carminic Acid 4.18 15.76 Alizarin Red S 2.48 2-3 11.97 2 Acid Blue 45 1.41 9.45 Acid Green 41 3.68 4 8.05 3-4 Mordant Yellow 12 12.56 2 18.56 2-3 Hematoxylin 5.45 8.17 Mordant Blue 9 3.63 9.80 Chromoxane Cyanine R 3.69 1-2 7.23 3 Calcon Carboxylic Acid 3.88 3 6.34 2 Plasmocorinth B 11.79 13.44 Pyrocatechol 4.59 5.74 Acid Alizarin Violet N 10.02 14.22 Alizarin Yellow GG 3 3 - These values indicate some color loss, which it is anticipated could be improved upon by refining the ink formulation, for example by altering the ratio of alumina oligomer:dye. As most commercially available dyes contain less than 100 percent colorant, another method would be to purify the dye, for example by using a known organic solvent extraction process.
- Textile ink compositions were prepared as described in example 1 and were spotted onto cotton and polyester fabrics. The fabrics were then washed in a domestic washing machine on the harshest washing cycle, using the recommended dosage of a domestic laundry detergent (TIDE® from Procter & Gamble, USA) and hot water (about 90 degrees Celsius) for up to 30 minutes. The color intensities and washfast values were calculated as described above, and the results that were obtained were similar to those in example 1. A skilled person will understand that this is a fairly harsh washfast test for any printed ink, and the results of this test are thus a good indication that the ink compositions are able to durably dye different fabrics.
- Textile ink compositions prepared according to example 1 were spotted onto a silk charmeuse fabric and allowed to dry. The washfastness was tested using the AATCC Washfast Test Method 61-2003 described above, and the fabric colors prior to and after the wash test were analyzed qualitatively (results not shown). The ink compositions were shown to dye silk fabric equally well.
- From the above examples, it can be seen that the applicant has utilized commercially available metal oxide oligomers and commercially available dyes to develop durable and washfast textile ink compositions that work equally well on silk, cotton and polyester fabrics.
- In addition to being able to durably dye more than one type of fabric, the ink compositions of the present invention are able to incorporate more dye than many other inks, are soluble and are therefore readily incorporated into inkjet inks, and do not have lightfast issues that are associated with other inks.
- While the invention has been described in detail with respect to specific embodiments thereof, it will be appreciated by those skilled in the art that various alterations, modifications and other changes may be made to the invention without departing from the spirit and scope of the present invention. It is therefore intended that the claims cover or encompass all such modifications, alterations and/or changes.
Claims (20)
1. A textile ink composition comprising a cationically charged metal oxide and a dye, wherein the composition is capable of dyeing at least two different types of fabric.
2. The composition of claim 1 , wherein the cationically charged metal oxide is an oligomer.
3. The composition of claim 1 , wherein the cationically charged metal oxide is a polymer.
4. The composition of claim 1 , wherein the cationically charged metal oxide is an alumina oligomer.
5. The composition of claim 4 , wherein the alumina oligomer is aluminum chlorohydrate.
6. The composition of claim 1 , wherein the dye has a substituent selected from the group consisting of anthraquinone, catechol, hydroxyazo and salicylic acid groups.
7. The composition of claim 6 , wherein the dye is selected from the group consisting of Carminic Acid, Alizarin Red, Acid Blue 45, Acid Green 41, Hematoxylin, Chromoxane Cyanine R, Calconcarboxylic Acid, Plasmocorinth B, Pyrocatechol, Acid Alizarin Violet N and Alizarin Yellow GG.
8. The composition of claim 1 , wherein the dye is a mordant dye.
9. The composition of claim 8 , wherein the mordant dye is selected from the group consisting of Mordant Yellow 12 and Mordant Blue 9.
10. The composition of claim 1 , wherein the ratio of metal oxide to dye ranges from about 1 metal oxide molecule per 10 dye molecules to about 10 metal oxide molecules per 1 dye molecule.
11. The composition of claim 1 , wherein the ratio of metal oxide to dye ranges from about 1 metal oxide molecule per 5 dye molecules to about 5 metal oxide molecules per 1 dye molecule.
12. The composition of claim 1 , wherein the ratio of metal oxide to dye is about 1 metal oxide molecule per 1 dye molecule.
13. The composition of claim 1 , which further includes one or more additives selected from the group consisting of polyols, viscosity modifiers, non-ionic surfactants, drying preventing agents, penetration accelerators, ultraviolet light absorbers, antioxidants, anti-fungal agents, pH adjusters, anti-foaming agents, dispersion aids, dispersion stabilizers, anti-rusting agents and chelating agents.
14. The composition of claim 1 , wherein the types of fabric are selected from the group consisting of cotton, silk, linen, rayon, nylon and polyester.
15. A method of manufacturing a textile ink composition that is capable of durably dyeing at least two different types of fabrics, the method comprising the step of mixing a cationically charged metal oxide with a dye.
16. The method of claim 15 , wherein the cationically charged metal oxide is an oligomer.
17. The method of claim 15 , wherein the cationically charged metal oxide is a polymer.
18. The method of claim 15 , wherein the cationically charged metal oxide is an alumina oligomer.
19. The method of claim 18 , wherein the alumina oligomer is aluminum chlorohydrate.
20. The method of claim 15 , wherein the dye has a substituent selected from the group consisting of anthraquinone, catechol, hydroxyazo and salicylic acid groups.
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PCT/US2005/011401 WO2006006969A1 (en) | 2004-06-30 | 2005-04-06 | Textile ink composition |
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