US20070100025A1 - Flexographic and gravure printing inks for nonwoven substrates - Google Patents
Flexographic and gravure printing inks for nonwoven substrates Download PDFInfo
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- US20070100025A1 US20070100025A1 US11/598,805 US59880506A US2007100025A1 US 20070100025 A1 US20070100025 A1 US 20070100025A1 US 59880506 A US59880506 A US 59880506A US 2007100025 A1 US2007100025 A1 US 2007100025A1
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Classifications
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- 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
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
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- 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
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
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- 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
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- 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
- C09D11/14—Printing inks based on carbohydrates
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- 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
- D06P1/46—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 using compositions containing natural macromolecular substances or derivatives thereof
- D06P1/48—Derivatives of carbohydrates
- D06P1/50—Derivatives of cellulose
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- 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
- D06P1/52—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 using compositions containing synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5285—Polyurethanes; Polyurea; Polyguanides
Definitions
- the invention relates to flexographic and/or rotogravure printing inks for non-woven substrates.
- U.S. Pat. No. 5,458,590 describes printing block urethane inks on nonwoven substrates for improved colorfastness and color transfer resistance.
- the block urethane ink system specifically mentioned is Parabond from Sun Chemical which is composed of a block urethane resin, vinyl resin, wax and epoxidized soybean oil along with pigments.
- U.S. Pat. No. 5,695,855 discloses adhesive inks for improved nonwoven products.
- U.S. Pat. No. 5,853,859 describes combining a latex polymer with pigment and a cure promoter for colorfastness when exposed to a wide range of pH liquids.
- International Publication Number WO 02/051644 A1 discloses a two part cross linked ink with a two part cross linked coating.
- a flexographic and/or rotogravure printing ink used on non-woven substrates comprised of solvent, colorant, polyurethane resin which provides a rub rating of at least 6, and optionally but preferably, nitrocellulose resin.
- a preferred polyurethane resin has a composition derived from a mixture of aliphatic and aromatic diisocyanates.
- the present invention provides a flexographic and/or rotogravure printing ink for use on non-woven substrates comprised of polyurethane resin, solvent, colorant, and optionally but preferably, nitrocellulose resin.
- any polyurethane resin which provides a rub rating of at least 6 for the formulation can be employed.
- the rub rating is at least 7 and most preferably at least 8.
- the rub rating is determined by printing the ink composition on a polyethylene/polypropylene nonwoven substrate, mounting the printed nonwoven substrate on a Sutherland Rub tester (manufactured by KVP Sutherland Paper Co. of Kalamazoo, Mich.) and rubbing it against a white linen swatch. Ten individuals rank how much color was transferred from the printed nonwoven substrate to the linen on a scale from 1-10, with ten being the highest (no color transfer) and one being the lowest (essentially complete transfer). The rub rating is the average of the ten ratings.
- One preferred class of polyurethane resin is those having a weight average molecular weight of at least 10,000, preferably at least about 20,000, more preferably at least about 23,000, and most preferably at least about 30,000.
- polyurethane resin is the reaction product of a mixture of at least one aliphatic isocyanate (preferably a diisocyanate) and at least one aromatic isocyanate (preferably a diisocyanate) with at least one isocyanate-reactive compound which may be, for instance, a diol, diamine or the like.
- this resin may be referred to as a semi-aliphatic polyurethane resin in this disclosure.
- the amount of aliphatic isocyanate component(s) is about 10% to about 90%, and preferably about 20% to about 80%.
- the amount of aromatic isocyanate component(s) is about 90% to about 10% of the total molar amount of isocyanate, and preferably about 20% to about 80%.
- the aliphatic isocyanate or diisocyanate includes both straight-chain aliphatic and branched chain aliphatic compounds as well as cycloaliphatic compounds.
- the isocyanate is a diisocyanate of 1 to about 10 carbon atoms.
- diisocyanates examples include 1,4-diisocyanatobutane, 1,6-diisocyanatohexane, 1,5-diisocyanato-2,2-dimethylpentane, 4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and 1,4-diisocyanatocyclo-hexane, 1-isocyanato-5-isocyanatomethyl-3,3,5-trimethylcyclohexane(isophorone diisocyanate or IPDI), 2,3-2, 4- and 2,6-diisocyanato-1-methylcyclohexane, 4,4 ′-and 2,4′-diisocyanatodicyclohexylmethane, 1-isocyanato-3-(4)-isocyanatomethyl-1-methyl-cyclohexane, 4,4′- and 2,4′-diisocyanatodiphenyl
- the aromatic isocyanate or diisocyanate is an isocyanate which contains an aromatic or cycloaromatic moiety, and may also contain aliphatic moieties.
- the isocyanate is a diisocyanate of 1 to about 10 carbon atoms.
- Examples of preferred diisocyanates are 1,1′-methylenebis[4-isocyanato-benzene (MDI), and 1,6-diisocyanato-hexane (HDI), toluene diisocyanate, and the like.
- TDI (1,3-diisocyanatomethyl-benzene) cannot be used for some applications due to regulatory restrictions.
- TDI is not comprised by the group of aromatic diisocyanates that are present in a molar amount between about 10% and about 90%, but TDI may be present in an incidental amount of below about 10% if permitted by the applicable regulations.
- the diol(s) which can be used to prepare the polyurethane resin of present invention are generally defined by the formula R(OH) 2 wherein R is a 2 to about 10 straight chain or branched chain hydrocarbon group. Preferably, R is an alkylene group of 2 to about 4 carbon atoms.
- R is a 2 to about 10 straight chain or branched chain hydrocarbon group.
- R is an alkylene group of 2 to about 4 carbon atoms.
- preferred diols include polyethylene glycol (PEG), polypropylene glycol (PPG) and polytetramethylene glycols (Poly-THF), 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, and mixtures thereof. According to the present invention, the use of PPG is particularly preferred.
- Diamines are a further isocyanate-reactive component which can be used to prepare the resin.
- the diamine can be any aliphatic, cycloaliphatic, aromatic, or heterocyclic diamine having primary or secondary amino groups.
- Example are ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, diaminobutane, hexamethylenediamine, 1,4-diaminocyclohexane, 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophorone diamine), m-xylene diamine or 1,3-bis (aminomethyl) cyclohexane.
- Yet another preferred class of polyurethane resin is semi-aliphatic resins having a weight average molecular weight of at least 20,000, and more preferably at least about 23,000, and most preferably at least about 30,000.
- the polyurethane resin may be present in an amount of between about 10 wt. % to about 60 wt. %. It is preferred that the polyurethane resin be present in an amount of between about 30 wt. % to about 40 wt. %.
- Suitable solvents in the ink of the present invention include highly active solvents and various combinations thereof.
- Such solvents include ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, alcohols, and the like, depending on the type of printing ink being prepared, i.e., either flexographic or gravure.
- the solvent be a combination of ester(s) and alcohol(s) in a ratio of about 1:99 to 99:1, preferably about 10:90 to 20:80.
- the total amount of solvent is generally about 1 to 70%, preferably about 10 to 50%, and most preferably about 20 to 40%.
- Suitable ester solvents include, but are not limited, to propyl acetate, ethyl acetate, butyl acetate, isopropyl acetate, propylene glycol monomethyl ether acetate and the like and combinations thereof. It is preferred that the ester solvent is propyl acetate.
- the ester solvent may be present in an amount of between about 1 wt. % to about 70 wt. %. It is preferred that the ester solvent be present in an amount of between about 10 wt. % to about 40 wt. % and most preferred between about 10 wt. % to about 20 wt. %
- Alcohol solvents include, but are not limited to, ethanol, propanol, ispropanol, glycol ethers, 1-ethoxy-2-propanol, propylene glycol n-propyl ether, dipropylene glycol, n-butyl ether, dipropylene glycol ethyl ether, diacetone alcohol, methyl amyl alcohol, diethylene glycol monobutyl ether, propylene glycol methyl ether and the like, and combinations thereof. It is preferred that the alcohol solvent is propanol or ethanol, and most preferred ethanol.
- the alcohol solvent may be present in an amount of between about 10 wt. % to about 70 wt. %. It is preferred that the alcohol solvent be present in an amount of between about 20 wt. % to about 60 wt. % and more preferred between about 40 wt. % to about 50 wt. %
- Suitable colorants include, but are not limited to, organic or inorganic pigments.
- Organic pigments may be one pigment or a combination of the following nonlimiting pigments: Pigment Yellows #12, 13, 14, 17, 74, 83; Pigment Reds #2, 22, 23, 48:1, 48:2, 52, 53, 57:1, 122, 166, 170, 266; Pigment Orange #5, 16, 34, 36; Blue #15:3, 15:4; Violet #3, 27; and/or Pigment Green #7.
- Inorganic pigments may be one of the following pigments: iron oxides, Pigment White #6, 7 and/or Pigment Black #7. These examples are illustrative only and other organic and inorganic pigments can be used as appropriate for the colors desired.
- the pigment may be present in an amount of between about 0.1 wt. % to about 20 wt. %. It is preferred that the pigment be present in an amount of between about 0.1 wt. % to about 10 wt. %.
- the printing ink also preferably includes nitrocellulose resin.
- Suitable nitrocellulose resins are those which are soluble in the composition and include, but are not limited to, a wide range of viscosity grades and solubility grades.
- the solubility grade may be one of the well-known grades such as AS (nitrogen content 10.7-11.3%), RS (nitrogen content 11.3-11.8%) and SS (nitrogen content 11.8-12.3%) and combinations thereof.
- AS nitrogen content 10.7-11.3%
- RS nitrogen content 11.3-11.8%
- SS nitrogen content 11.8-12.3%
- the viscosity range may be between about 1/16second and 5 seconds as measured by steel ball drop test. It is preferred that the nitrocellulose have a viscosity between about 1 ⁇ 8to 1 ⁇ 4second.
- the nitrocellulose resin is solubility grade SS with viscosity of about 1 ⁇ 8second.
- the nitrocellulose resin may be in an amount up to about 15 wt. %, preferably between about 1 wt. % to about 10 wt. %, and most preferably in an amount of between about 1.0 wt. % to about 4.0 wt. %
- the printing ink may also include waxes such as, but not limited to, amide wax, erucamide wax, polypropylene wax, paraffin wax, polyethylene wax, Teflon, carnauba wax and the like.
- the wax may be a combination of waxes. It is preferred that the wax be a blend of amide and erucamide waxes.
- the wax if present, is in an amount of up to about 4 wt. %. When present, it is preferred that the wax be an amount of between about 0.1 wt. % to about 2 wt. %.
- additives alone or in combination may be employed, including but not limited to other resins, titanates, ammonia, defoamers, stabilizers, silicones, plasticizers and the like.
- the components of the printing ink may be mixed in any order of components.
- a pigment dispersion is combined with an ink vehicle containing resins and solvents.
- Another example is providing a pigment dispersion created by combining the pigment with nitrocellulose resin, ester solvent and alcohol solvent and then combining this dispersion with a polyurethane resin.
- the printing ink imparts excellent color transfer resistance when printed on nonwoven substrates.
- the nonwoven substrate may be comprised of a polyethylene film, a polypropylene films, polyester films, nylon and the like, as well as combinations thereof. It is preferred that the nonwovens substrate be polyethylene or polypropylene.
- the non-woven may also be comprised of polymers, copolymers, natural fibers, as well as air laid, we laid, solution spun fiber webs, and the like.
- the printing ink may be printed onto the nonwoven substrate via either flexographic or rotogravure (direct or indirect) printing process.
- the printed ink may be found on a variety of products including but not limited to personal care products, such as diapers, training pants, wipes, feminine pads, adult incontinence garments, hospital/medical gowns and related products, and clothing such as workwear and cleaning garments, and the like.
- the printing inks of the present invention are further illustrated by the following non-limiting examples in which all parts and percentages are by weight, and temperatures in degrees Centigrade, unless otherwise indicated.
- a printing ink was prepared using SS 20 IPA Wet as the nitrocellulose resin, the semi-aliphatic reaction product of TDI, MDI and PPG having a molecular weight of approximately 81,000 as polyurethane resin A, and Irgalite Blue GLVO as the pigment, according to the following formula: TABLE 1 Component Weight percent Nitrocellulose resin 1.0 Polyurethane resin A 35.0 Propyl acetate 12.0 Ethanol 47.0 Pigment 5.0 TOTAL 100.0
- SS 20 IPA Wet was used as the nitrocellulose in all inks except 2-D which employed a combination of 2.4 parts of SS 20 IPA Wet (Isochem North America LLC) and 2.8 parts (based on 100 part ink) of 1 ⁇ 4′′ SS of Votoatim International.
- Polyurethane resin B is the semi-aliphatic reaction product of various diols of different molecular weight.
- Inks were prepared containing 2.4 parts of SS 20 IPA Wet nitrocellulose resin, 35 parts polyurethane, 10.6 parts of propyl acetate, 47 parts of ethanol and 5 parts of colorant (52 DT 913 pigment dispersion, CDR Pigments & Dispersions, Elizabethtown, N.J.).
- Polyurethanes C, D and E are polyetherpolyol-based aliphatic polyurethane resin of different softness with D being softer than C and E being harder than C;
- polyurethane F is a hydroxyl functional aliphatic polyurethane resin;
- G is an amide-urethane hybrid aliphatic polyurethane resin; and H is a nitrocellulose compatible aliphatic polyurethane resin.
- Example 1 The ink of Example 1 was compared to various conventional ink formulations by testing according to the method of Example 2.
- Ink 4-A is a conventional flexographic printing ink used for surface printing, while 4-B is a conventional gravure printing ink for lamination printing.
- Inks 4-C, 4-D and 4-E are conventional flexographic printing inks for lamination printing and 4-F is a flexographic and gravure ink for surface or lamination printing.
- Phenolic resin Beckacite 004-01, Reichhold of Durham, NC h Styrenated acrylic, Reactol 100, Lawter International of Pleasant Prairie, WI i Styrene/maleic anhydride polymer, SMA 17352G, Sartomer Co of Exton, PA j Rosin acrylic solution, TV94-5991, Sun Chemical Corporation of Parsippany, NJ k R2764-133, Lubrizol Dock Resins of Linden NJ, l Irgalite Blue GLVO m B15:3 surfactant/acrylic dispersion, BCD ⁇ 9730 , Sun Chemical Corporation of Parsippany, NJ.
- a printing ink was prepared according to the following formula: TABLE 5 Component Weight percent Polyurethane resin A 55.0 Propyl acetate 12.0 Ethanol 25.0 Pigment (Irgalite Blue GLVO) 8.0 TOTAL 100.0
- Printing inks are prepared according to the following formulae: TABLE 6 Component Weight percent Polyurethane resin B 57.0 53.0 46.0 Butyl acetate 42.0 12.0 Diethylene glycol 27.0 45.0 monobutyl ether Pigment White #6 5.0 8.0 9.0 TOTAL 100.0 100.0 100.0
- Ink compositions were prepared in accordance with the formulations of Examples 1 and 5 with polyurethanes of different molecular weights and tested for rub resistance.
- the polyurethanes, approximate molecular weights and rub results are set forth in Table 7.
- Polyurethane I is the reaction product of MDI and PPG; J is the reaction product of mixture of TDI and IPDI with PPG; K is the reaction product of IPDI and PPG; and L is the reaction product of a mixture of MDI and IPDI with PPG.
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Abstract
A flexographic and/or rotogravure printing ink used on non-woven substrates contains polyurethane resin, solvent, and colorant.
Description
- This is a continuation-in-part of application Ser. No. 11/265,760, filed Nov. 2, 2005.
- The invention relates to flexographic and/or rotogravure printing inks for non-woven substrates.
- There are many different incontinence disposable child and adult care products on the market including diapers, training under pants, and temporary swimsuits. Many of these products are constructed with nonwoven substrates including but not limited to nonwoven polyethylene or nonwoven polypropylene films. There is a desire within the marketplace to print graphics on these nonwoven substrates for appearance such as mere decoration or for utility such as indication of wetness. These substrates are typically printed with flexographic or rotogravure presses for these products, however, the printed inks have low color transfer resistance so as to discolor anything the nonwoven substrate may come into contact with such as clothing, carpet and furniture. The nonwoven substrate is not porous such as paper and thus the printed ink easily transfers from the substrate onto contact substrates/objects. Thus, there is a desire for the printed graphics on nonwoven substrates to have augmented color transfer resistance properties.
- U.S. Pat. No. 5,458,590 describes printing block urethane inks on nonwoven substrates for improved colorfastness and color transfer resistance. The block urethane ink system specifically mentioned is Parabond from Sun Chemical which is composed of a block urethane resin, vinyl resin, wax and epoxidized soybean oil along with pigments. U.S. Pat. No. 5,695,855 discloses adhesive inks for improved nonwoven products. U.S. Pat. No. 5,853,859 describes combining a latex polymer with pigment and a cure promoter for colorfastness when exposed to a wide range of pH liquids. International Publication Number WO 02/051644 A1 discloses a two part cross linked ink with a two part cross linked coating.
- However, none of the existing inks provide for use of conventional flexographic or rotogravure printing inks on nonwoven substrates having the same properties of enhanced color transfer resistance as on other substrates. Accordingly, a need exists for an ink which can be used in both flexographic or rotogravure printing on nonwoven substrates while exhibiting and maintaining enhanced color transfer resistance properties.
- It has now been found that the above objectives can be realized by a flexographic and/or rotogravure printing ink used on non-woven substrates comprised of solvent, colorant, polyurethane resin which provides a rub rating of at least 6, and optionally but preferably, nitrocellulose resin. A preferred polyurethane resin has a composition derived from a mixture of aliphatic and aromatic diisocyanates.
- Other objects and advantages of the present invention will become apparent from the following description and appended claims.
- The present invention provides a flexographic and/or rotogravure printing ink for use on non-woven substrates comprised of polyurethane resin, solvent, colorant, and optionally but preferably, nitrocellulose resin.
- Any polyurethane resin which provides a rub rating of at least 6 for the formulation can be employed. Preferably, the rub rating is at least 7 and most preferably at least 8. The rub rating is determined by printing the ink composition on a polyethylene/polypropylene nonwoven substrate, mounting the printed nonwoven substrate on a Sutherland Rub tester (manufactured by KVP Sutherland Paper Co. of Kalamazoo, Mich.) and rubbing it against a white linen swatch. Ten individuals rank how much color was transferred from the printed nonwoven substrate to the linen on a scale from 1-10, with ten being the highest (no color transfer) and one being the lowest (essentially complete transfer). The rub rating is the average of the ten ratings.
- One preferred class of polyurethane resin is those having a weight average molecular weight of at least 10,000, preferably at least about 20,000, more preferably at least about 23,000, and most preferably at least about 30,000.
- Another preferred class of polyurethane resin is the reaction product of a mixture of at least one aliphatic isocyanate (preferably a diisocyanate) and at least one aromatic isocyanate (preferably a diisocyanate) with at least one isocyanate-reactive compound which may be, for instance, a diol, diamine or the like. For convenience, this resin may be referred to as a semi-aliphatic polyurethane resin in this disclosure. Of the total molar quantity of isocyanate, the amount of aliphatic isocyanate component(s) is about 10% to about 90%, and preferably about 20% to about 80%. Accordingly, the amount of aromatic isocyanate component(s) is about 90% to about 10% of the total molar amount of isocyanate, and preferably about 20% to about 80%.
- The aliphatic isocyanate or diisocyanate includes both straight-chain aliphatic and branched chain aliphatic compounds as well as cycloaliphatic compounds. Preferably, the isocyanate is a diisocyanate of 1 to about 10 carbon atoms. Examples of preferred diisocyanates are 1,4-diisocyanatobutane, 1,6-diisocyanatohexane, 1,5-diisocyanato-2,2-dimethylpentane, 4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and 1,4-diisocyanatocyclo-hexane, 1-isocyanato-5-isocyanatomethyl-3,3,5-trimethylcyclohexane(isophorone diisocyanate or IPDI), 2,3-2, 4- and 2,6-diisocyanato-1-methylcyclohexane, 4,4 ′-and 2,4′-diisocyanatodicyclohexylmethane, 1-isocyanato-3-(4)-isocyanatomethyl-1-methyl-cyclohexane, 4,4′- and 2,4′-diisocyanatodiphenylmethane, and mixtures thereof, or 2,2,4- or 2,4,4 trimethyldiisocyanatohexane (TMDI).
- The aromatic isocyanate or diisocyanate is an isocyanate which contains an aromatic or cycloaromatic moiety, and may also contain aliphatic moieties. Preferably, the isocyanate is a diisocyanate of 1 to about 10 carbon atoms. Examples of preferred diisocyanates are 1,1′-methylenebis[4-isocyanato-benzene (MDI), and 1,6-diisocyanato-hexane (HDI), toluene diisocyanate, and the like.
- For some applications, TDI (1,3-diisocyanatomethyl-benzene) cannot be used for some applications due to regulatory restrictions. For such applications, TDI is not comprised by the group of aromatic diisocyanates that are present in a molar amount between about 10% and about 90%, but TDI may be present in an incidental amount of below about 10% if permitted by the applicable regulations.
- The diol(s) which can be used to prepare the polyurethane resin of present invention are generally defined by the formula R(OH)2 wherein R is a 2 to about 10 straight chain or branched chain hydrocarbon group. Preferably, R is an alkylene group of 2 to about 4 carbon atoms. Examples of preferred diols include polyethylene glycol (PEG), polypropylene glycol (PPG) and polytetramethylene glycols (Poly-THF), 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, and mixtures thereof. According to the present invention, the use of PPG is particularly preferred.
- Diamines are a further isocyanate-reactive component which can be used to prepare the resin. The diamine can be any aliphatic, cycloaliphatic, aromatic, or heterocyclic diamine having primary or secondary amino groups. Example are ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, diaminobutane, hexamethylenediamine, 1,4-diaminocyclohexane, 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophorone diamine), m-xylene diamine or 1,3-bis (aminomethyl) cyclohexane.
- Yet another preferred class of polyurethane resin is semi-aliphatic resins having a weight average molecular weight of at least 20,000, and more preferably at least about 23,000, and most preferably at least about 30,000.
- The polyurethane resin may be present in an amount of between about 10 wt. % to about 60 wt. %. It is preferred that the polyurethane resin be present in an amount of between about 30 wt. % to about 40 wt. %.
- Suitable solvents in the ink of the present invention include highly active solvents and various combinations thereof. Such solvents include ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, alcohols, and the like, depending on the type of printing ink being prepared, i.e., either flexographic or gravure. It is preferred that the solvent be a combination of ester(s) and alcohol(s) in a ratio of about 1:99 to 99:1, preferably about 10:90 to 20:80. The total amount of solvent is generally about 1 to 70%, preferably about 10 to 50%, and most preferably about 20 to 40%.
- Suitable ester solvents include, but are not limited, to propyl acetate, ethyl acetate, butyl acetate, isopropyl acetate, propylene glycol monomethyl ether acetate and the like and combinations thereof. It is preferred that the ester solvent is propyl acetate. The ester solvent may be present in an amount of between about 1 wt. % to about 70 wt. %. It is preferred that the ester solvent be present in an amount of between about 10 wt. % to about 40 wt. % and most preferred between about 10 wt. % to about 20 wt. %
- Alcohol solvents include, but are not limited to, ethanol, propanol, ispropanol, glycol ethers, 1-ethoxy-2-propanol, propylene glycol n-propyl ether, dipropylene glycol, n-butyl ether, dipropylene glycol ethyl ether, diacetone alcohol, methyl amyl alcohol, diethylene glycol monobutyl ether, propylene glycol methyl ether and the like, and combinations thereof. It is preferred that the alcohol solvent is propanol or ethanol, and most preferred ethanol. The alcohol solvent may be present in an amount of between about 10 wt. % to about 70 wt. %. It is preferred that the alcohol solvent be present in an amount of between about 20 wt. % to about 60 wt. % and more preferred between about 40 wt. % to about 50 wt. %
- Suitable colorants include, but are not limited to, organic or inorganic pigments. Organic pigments may be one pigment or a combination of the following nonlimiting pigments: Pigment Yellows #12, 13, 14, 17, 74, 83; Pigment Reds #2, 22, 23, 48:1, 48:2, 52, 53, 57:1, 122, 166, 170, 266; Pigment Orange #5, 16, 34, 36; Blue #15:3, 15:4; Violet #3, 27; and/or Pigment Green #7. Inorganic pigments may be one of the following pigments: iron oxides, Pigment White #6, 7 and/or Pigment Black #7. These examples are illustrative only and other organic and inorganic pigments can be used as appropriate for the colors desired. The pigment may be present in an amount of between about 0.1 wt. % to about 20 wt. %. It is preferred that the pigment be present in an amount of between about 0.1 wt. % to about 10 wt. %.
- The printing ink also preferably includes nitrocellulose resin. Suitable nitrocellulose resins are those which are soluble in the composition and include, but are not limited to, a wide range of viscosity grades and solubility grades. For example, the solubility grade may be one of the well-known grades such as AS (nitrogen content 10.7-11.3%), RS (nitrogen content 11.3-11.8%) and SS (nitrogen content 11.8-12.3%) and combinations thereof. It is preferred that the nitrocellulose resin is solubility grade SS. The viscosity range may be between about 1/16second and 5 seconds as measured by steel ball drop test. It is preferred that the nitrocellulose have a viscosity between about ⅛to ¼second. It is more preferred that the nitrocellulose resin is solubility grade SS with viscosity of about ⅛second. When present, the nitrocellulose resin may be in an amount up to about 15 wt. %, preferably between about 1 wt. % to about 10 wt. %, and most preferably in an amount of between about 1.0 wt. % to about 4.0 wt. %
- The printing ink may also include waxes such as, but not limited to, amide wax, erucamide wax, polypropylene wax, paraffin wax, polyethylene wax, Teflon, carnauba wax and the like. The wax may be a combination of waxes. It is preferred that the wax be a blend of amide and erucamide waxes. The wax, if present, is in an amount of up to about 4 wt. %. When present, it is preferred that the wax be an amount of between about 0.1 wt. % to about 2 wt. %.
- As with many printing inks, other additives, alone or in combination may be employed, including but not limited to other resins, titanates, ammonia, defoamers, stabilizers, silicones, plasticizers and the like.
- The components of the printing ink may be mixed in any order of components. Typically, a pigment dispersion is combined with an ink vehicle containing resins and solvents. Another example is providing a pigment dispersion created by combining the pigment with nitrocellulose resin, ester solvent and alcohol solvent and then combining this dispersion with a polyurethane resin.
- The printing ink imparts excellent color transfer resistance when printed on nonwoven substrates. The nonwoven substrate may be comprised of a polyethylene film, a polypropylene films, polyester films, nylon and the like, as well as combinations thereof. It is preferred that the nonwovens substrate be polyethylene or polypropylene. The non-woven may also be comprised of polymers, copolymers, natural fibers, as well as air laid, we laid, solution spun fiber webs, and the like.
- The printing ink may be printed onto the nonwoven substrate via either flexographic or rotogravure (direct or indirect) printing process. The printed ink may be found on a variety of products including but not limited to personal care products, such as diapers, training pants, wipes, feminine pads, adult incontinence garments, hospital/medical gowns and related products, and clothing such as workwear and cleaning garments, and the like.
- The printing inks of the present invention are further illustrated by the following non-limiting examples in which all parts and percentages are by weight, and temperatures in degrees Centigrade, unless otherwise indicated.
- A printing ink was prepared using SS 20 IPA Wet as the nitrocellulose resin, the semi-aliphatic reaction product of TDI, MDI and PPG having a molecular weight of approximately 81,000 as polyurethane resin A, and Irgalite Blue GLVO as the pigment, according to the following formula:
TABLE 1 Component Weight percent Nitrocellulose resin 1.0 Polyurethane resin A 35.0 Propyl acetate 12.0 Ethanol 47.0 Pigment 5.0 TOTAL 100.0 - Various inks were prepared and tested for rub resistance, which represents the resistance to color transfer from the nonwoven substrate. In this test, each ink was printed on a composite polyethylene/propylene nonwoven substrate and visually observed for color transference. The printed nonwoven substrate was mounted on a Sutherland Rub tester (manufactured by KVP Sutherland Paper Co. of Kalamazoo, Mich.) rubbed against a white linen swatch and evaluated by ten individuals for how much color was transferred from the printed nonwoven substrate to the linen. The inks were then ranked from 1-10, with ten being the highest or best ranking, for color transfer resistance which is exhibited by the least amount of color transferred onto the white 10 linen swatch, and an average value calculated. A rank of 6 or greater was deemed acceptable meaning the composition is color transfer resistant. Preferably, the rank is at least 7 and most preferably at least 8. For convenience, the values in the tables herein have been rounded to the nearest integer.
- The composition and results are set forth in Table 2 below. SS 20 IPA Wet was used as the nitrocellulose in all inks except 2-D which employed a combination of 2.4 parts of SS 20 IPA Wet (Isochem North America LLC) and 2.8 parts (based on 100 part ink) of ¼″ SS of Votoatim International. Polyurethane resin B is the semi-aliphatic reaction product of various diols of different molecular weight.
TABLE 2 Ink Ink Ink Ink Ink Ink Ink Ink Ink Ink Ink Component 2-A 2-B 2-C 2-D 2-E 2-F 2-G 2-H 2-I 2-J 2-K Nitrocellulose 2.4 2.4 1 5.2 2.4 2.4 2.4 2.4 2.4 2.4 2.4 resin Polyurethane 35 35 35 35 35 resin A Polyurethane 35 35 35 35 35 35 resin B Propyl acetate 10.6 10.6 12 10.6 10.6 10.6 10.6 10.6 10.6 10.6 10.6 Ethanol 42 47 47 44.2 46 44 42 47 44.2 46 44 Coloranta 5 5 5 5 5 5 5 5 5 5 5 Siliconeb 0 0 0 0 1 0 0 0 0 1 0 Ti phosphate 0 0 0 0 0 3 0 0 0 0 3 comlexc Waxd 5 0 0 0 0 0 5 0 0 0 0 TOTAL 100 100 100 100 100 100 100 100 100 100 100 Rub test rating 9 7 8 6 7 7 8 8 7 8 8 (1-10)
aDispersion of B15:3 pigment and nitrocellulose, 52 DT 913 dispersion, CDR Pigments & Dispersions of Elizabethtown, NJ.
bDOW 51, DOW Chemical of Midland, MI.
cVertec IA-10, Johnson Matthey Catalysts of Cleveland U.K.
derucamide/stearamide wax blend 11-K-14, Sun Chemical Corporation of Parsippany, NJ.
- Inks were prepared containing 2.4 parts of SS 20 IPA Wet nitrocellulose resin, 35 parts polyurethane, 10.6 parts of propyl acetate, 47 parts of ethanol and 5 parts of colorant (52 DT 913 pigment dispersion, CDR Pigments & Dispersions, Elizabethtown, N.J.). Polyurethanes C, D and E are polyetherpolyol-based aliphatic polyurethane resin of different softness with D being softer than C and E being harder than C; polyurethane F is a hydroxyl functional aliphatic polyurethane resin; G is an amide-urethane hybrid aliphatic polyurethane resin; and H is a nitrocellulose compatible aliphatic polyurethane resin.
- Each ink was printed on a composite polyethylene/propylene nonwoven substrate and visually observed for color transference pursuant to the test method of Example 2. The composition and results are set forth in Table 3 below.
TABLE 3 3-A 3-B 3-C 3-D 3-E 3-F 3-G 3-H Polyurethane B C D E F G H A resin Rub test 7 6 5 5 6 1 6 8 rating (1-10) - The ink of Example 1 was compared to various conventional ink formulations by testing according to the method of Example 2. Ink 4-A is a conventional flexographic printing ink used for surface printing, while 4-B is a conventional gravure printing ink for lamination printing. Inks 4-C, 4-D and 4-E are conventional flexographic printing inks for lamination printing and 4-F is a flexographic and gravure ink for surface or lamination printing.
TABLE 4 Example Comparative Ink Component 1 Ink 4-A 4-B 4-C 4-D 4-E 4-F Nitrocellulose 1.0 8.45 13.83 0 0 0 0 resin (2.38a + 6.07b) (4.13a + 9.7b) polyurethane 35 5.6c 4d 19.25e 19.25e 27e 50f resin Acrylic resin 0 5.6g 2.0h 0 7.5i 9.0j 0 Polyester 0 0 0 19.25 13.75 0 0 resink Propyl 12 18.6 29.3 0 0 0 acetate Ethanol 47 40.24 40.32 5 1.25 7.29 0 Water 0 0 0 6 5 1.71 0 Pigment 5 15.75l 8.55l 50m 50m 50m 50m Wax 0 2.0n 0 0 0 0 0 Additives 0 1.2o + 0.4p + 0.16q + 2.0r 0 1.25s + 1.25t 1.25s + 1.25t + 2.5u 5.0v 0 TOTAL 100 100 100 100 100 100 100 Rub test 9 2 3 3 3 2 1 rating (1-10, 10 highest)
a¼″ SS nitrocellulose, Votoratim International of Curacao Netherlands Antilles.
b30-35 SS nitrocellulose, Nobel Trading of Duncanville, TX.
caliphatic polyurethane resin
daliphatic polyurethane resin
ealiphatic polyurethane resin
faliphatic polyurethane resin.
gPhenolic resin, Beckacite 004-01, Reichhold of Durham, NC
hStyrenated acrylic, Reactol 100, Lawter International of Pleasant Prairie, WI
iStyrene/maleic anhydride polymer, SMA 17352G, Sartomer Co of Exton, PA
jRosin acrylic solution, TV94-5991, Sun Chemical Corporation of Parsippany, NJ
kR2764-133, Lubrizol Dock Resins of Linden NJ,
lIrgalite Blue GLVO
mB15:3 surfactant/acrylic dispersion, BCD−9730, Sun Chemical Corporation of Parsippany, NJ.
nSST-3 Teflon, Shamrock Technologies of Newark, NJ
oVertec IA-10, Johnson Matthey Catalysts of Cleveland U.K., titanate.
pBisamid waw, Printwax A70 Pulver, Deurex Micro Technology, Troglitz Germany.
qPolydimethlysiloxane, DC-200 Fluid, DOW Chemical of Midland, MI., silicone.
rHydrogenated rosin ester, Hercolyn D, Chemcentral of Bedford, IL, plasticizer.
sPolyglycol ester silica blend, Nalco 2303, Nalco Chemical of Naperville, IL, defoamer.
tParaffinic blend, Dapro DF-975, Elementis Specialites of Highstown, NJ, defoamer.
uSorbitol solution, Univar of Kirkland, WA, defoamer.
vClay, ASP 600, A.E. Fleming of Warren, MI, clay.
- A printing ink was prepared according to the following formula:
TABLE 5 Component Weight percent Polyurethane resin A 55.0 Propyl acetate 12.0 Ethanol 25.0 Pigment (Irgalite Blue GLVO) 8.0 TOTAL 100.0 - Printing inks are prepared according to the following formulae:
TABLE 6 Component Weight percent Polyurethane resin B 57.0 53.0 46.0 Butyl acetate 42.0 12.0 Diethylene glycol 27.0 45.0 monobutyl ether Pigment White #6 5.0 8.0 9.0 TOTAL 100.0 100.0 100.0 - Ink compositions were prepared in accordance with the formulations of Examples 1 and 5 with polyurethanes of different molecular weights and tested for rub resistance. The polyurethanes, approximate molecular weights and rub results are set forth in Table 7.
TABLE 7 Ex. 1 Formula Ex. 1 Formula Polyurethane Molecular Weight Rub Rating Rub Rating I 7,000 2 2 J 35,000 6 8 K 23,000 7 7 L 59,700 8 9 A 81,000 8 9
Polyurethane I is the reaction product of MDI and PPG; J is the reaction product of mixture of TDI and IPDI with PPG; K is the reaction product of IPDI and PPG; and L is the reaction product of a mixture of MDI and IPDI with PPG. - The invention has been described in terms of preferred embodiments thereof, but is more broadly applicable as will be understood by those skilled in the art. The scope of the invention is only limited by the following claims.
Claims (30)
1. A printing ink comprising:
a. polyurethane resin having a rub rating of at least 6;
b. organic solvent; and
c. colorant.
2. The printing ink of claim 1 wherein the polyurethane resin is the reaction product of a mixture of at least one aliphatic diisocyanate and at least one aromatic diisocyanate with at least one isocyanate-reactive compound.
3. The printing ink of claim 1 wherein the polyurethane resin has a molecular weight of at least 10,000.
4. The printing ink of claim 1 wherein the polyurethane resin is present in an amount of about 10 wt. % and about 60 wt. %, the solvent is present in an amount of about 1 wt. % and about 70 wt. %, and the colorant is present in an amount of about 0.1 wt. % and about 20 wt. %
5. The printing ink of claim 4 wherein the solvent is an ester, an alcohol or a combination thereof.
6. The printing ink of claim 5 , wherein the ester solvent is selected from the group consisting of propyl acetate, ethyl acetate, butyl acetate, isopropyl acetate, propylene glycol monomethyl ether acetate, and combinations thereof; and the alcohol solvent is selected from the group consisting of ethanol, propanol, isopropanol, 1-ethocy-2-propanol, propylene glycol n-propyl ether, dipropylene glycol, n-butyl ether, diacetone alcohol, methyl amyl alcohol, and combinations thereof.
7. The printing ink of claim 6 wherein the ester solvent is present in an amount of about 10 wt. % and about 40 wt. % and the alcohol solvent is present in an amount of between 10 wt. % and about 70 wt. %.
8. The printing ink of claim 7 wherein the ester solvent comprises propyl acetate, ethanol or a combination thereof.
9. The printing ink of claim 8 wherein the alcohol solvent is present in an amount of between 20 wt. % and about 60 wt. %, the polyurethane resin has a molecular weight of at least about 23,000 and is present in an amount of about 30 wt. % and about 40 wt. %, and the colorant is present in an amount of between 0.1 wt. % and about 10 wt. %.
10. The printing ink of claim 9 wherein the colorant is a pigment is selected from the group consisting of Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 74, Pigment Yellow 83, Pigment Red 2, Pigment Red 22, Pigment Red 23, Pigment Red 48:1, Pigment Red 48:2, Pigment Red 52, Pigment Red 53, Pigment Red 57:1, Pigment Red 122, Pigment Red 166, Pigment Red 170, Pigment Red 266, Pigment Orange 5, Pigment Orange 16, Pigment Orange 34, Pigment Orange 36, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Violet 3, Pigment Violet 27, Pigment Green 7, iron oxides, Pigment White 6, Pigment White 7, and Pigment Black 7, and combinations thereof.
11. The printing ink of claim 4 further comprising a wax selected from the group consisting of amide wax, erucamide wax, polypropylene wax, paraffin wax, polyethylene wax, polyethylene terephthalate, carnauba wax and combinations thereof in an amount of 4 wt. % or less.
12. The printing ink of claim 11 wherein the wax is present in an amount of about 0.1 wt. % to about 2 wt. %.
13. The printing ink of claim 1 further comprising an amount of nitrocellulose resin which does not exceed 15 wt. %.
14. The printing ink of claim 1 further comprising nitrocellulose resin of solubility grade SS in an amount about 1 wt. % and about 10 wt. %; and wherein the solvent is an ester, an alcohol or a combination thereof and is present in an amount of about 1 wt. % and about 70 wt. %.
15. The printing ink of claim 14 wherein the nitrocellulose resin is present in an amount about 0.1 wt. % and about 4 wt. %, and wherein the polyurethane resin has a molecular weight of at least 20,000 and is present in an amount of about 30 wt. % and about 40 wt. %; and the solvent is a combination of ester and alcohol in a total amount of about 10 wt. % to 40 wt. %.
16. The printing ink of claim 15 wherein the colorant is selected from the group consisting of organic and inorganic pigments and is present in an amount of between 0.1 wt. % and about 20 wt. %; the polyurethane resin is a semi-aliphatic resin having a molecular weight of at least about 23,000; and the ink further comprises wax in an amount up to about 4 wt. %.
17. The printing ink of claim 16 wherein the colorant is present in an amount of between 0.1 wt. % and about 1 wt. %; and the wax is present in an amount of about 0.1 wt. % to 2 wt. %.
18. In a method of flexographic printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 16 as said ink.
19. In a method of flexographic printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 3 as said ink.
20. In a method of flexographic printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 2 as said ink.
21. In a method of flexographic printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 1 as said ink.
22. In a method of rotogravure printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 1 as said ink.
23. In a method of rotogravure printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 2 as said ink.
24. In a method of flexographic printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 3 as said ink.
25. In a method of rotogravure printing in which an ink is applied to a substrate, the improvement which comprises employing the ink of claim 16 as said ink.
26. A nonwoven substrate printed with the printing ink of claim 1 .
27. A nonwoven substrate printed with the printing ink of claim 2 .
28. A nonwoven substrate printed with the printing ink of claim 3 .
29. A nonwoven substrate printed with the printing ink of claim 16 .
30. The nonwoven substrate of claim 27 in which the substrate is selected from the group consisting of polyethylene, polypropylene, polyester, nylon and combinations thereof.
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- 2006-11-02 CN CNA2006800411638A patent/CN101300316A/en active Pending
- 2006-11-02 EP EP06839679A patent/EP1954769B1/en active Active
- 2006-11-14 US US11/598,805 patent/US20070100025A1/en not_active Abandoned
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2013
- 2013-05-27 JP JP2013110768A patent/JP2013231179A/en active Pending
Cited By (14)
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CN101874086A (en) * | 2007-10-31 | 2010-10-27 | 太阳化学公司 | Flexographic and gravure printing inks for nonwoven substrates |
US20100189968A1 (en) * | 2007-10-31 | 2010-07-29 | Diane Steiner | Flexographic and gravure printing inks for nonwoven substrates |
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US8608843B2 (en) * | 2007-12-28 | 2013-12-17 | Eckart Gmbh | Pigment preparation and ink jet printing ink |
US20130088553A1 (en) * | 2007-12-28 | 2013-04-11 | Eckart Gmbh | Pigment preparation and ink jet printing ink |
US8216666B2 (en) | 2008-02-29 | 2012-07-10 | The Procter & Gamble Company | Substrates having improved crockfastness |
US20090221736A1 (en) * | 2008-02-29 | 2009-09-03 | Mccurry Charles Douglas | Water-based ink composition for improved crockfastness |
US8673430B2 (en) | 2008-02-29 | 2014-03-18 | Alrick Vincent Warner | Substrates having improved crockfastness |
US9283794B2 (en) | 2008-02-29 | 2016-03-15 | The Procter & Gamble Company | Substrates having improved crockfastness |
US9770373B2 (en) | 2008-02-29 | 2017-09-26 | The Procter & Gamble Company | Substrates having improved crockfastness |
US10836196B2 (en) | 2008-02-29 | 2020-11-17 | The Procter & Gamble Company | Substrates having improved crockfastness |
ITSA20080020A1 (en) * | 2008-07-29 | 2008-10-28 | Besafilm S R L | POLYPROPYLENE WITH SCENTED ESSENCES |
WO2010114899A1 (en) | 2009-03-31 | 2010-10-07 | Sun Chemical Corporation | Substrate printed with a water-based urethane printing ink with improved performance properties |
CN110724408A (en) * | 2019-11-19 | 2020-01-24 | 成都普瑞斯特新材料有限公司 | Universal U-shaped white ink for shrink film and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN104277583A (en) | 2015-01-14 |
JP2009515013A (en) | 2009-04-09 |
US20080255275A1 (en) | 2008-10-16 |
CN101300316A (en) | 2008-11-05 |
KR20140016424A (en) | 2014-02-07 |
JP2013231179A (en) | 2013-11-14 |
KR20080069668A (en) | 2008-07-28 |
EP1954769B1 (en) | 2012-08-22 |
US8383699B2 (en) | 2013-02-26 |
WO2007056660A1 (en) | 2007-05-18 |
PL1954769T3 (en) | 2013-03-29 |
EP1954769A1 (en) | 2008-08-13 |
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Owner name: SUN CHEMICAL CORPORATION, NEW JERSEY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:STEINER, DIANE;DEBARTOLO, TOM;WILLIAMS, JR., CHARLES B.;REEL/FRAME:018603/0158 Effective date: 20061113 |
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STCB | Information on status: application discontinuation |
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