WO1990012067A1 - Composition contenant des colorants lavables - Google Patents

Composition contenant des colorants lavables Download PDF

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Publication number
WO1990012067A1
WO1990012067A1 PCT/US1990/001939 US9001939W WO9012067A1 WO 1990012067 A1 WO1990012067 A1 WO 1990012067A1 US 9001939 W US9001939 W US 9001939W WO 9012067 A1 WO9012067 A1 WO 9012067A1
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WO
WIPO (PCT)
Prior art keywords
composition
dye
weight
amount
dyes
Prior art date
Application number
PCT/US1990/001939
Other languages
English (en)
Inventor
Richard E. Miller
Original Assignee
Binney & Smith Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Binney & Smith Inc. filed Critical Binney & Smith Inc.
Publication of WO1990012067A1 publication Critical patent/WO1990012067A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D11/16—Writing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/06—Artists' paints

Definitions

  • This invention relates generally to the field of water soluble coloring materials for drawing, painting, and coloring purposes, such as marker inks and paints.
  • the invention relates to marking instruments containing liquid inks, and it more specifically relates to the formulation of inks for use in marking pens or, simply, markers.
  • the invention relates to improvements in coloring and drawing markers for use by young children.
  • inks which are aqueous solutions of dyes known in the trade as "acid dyes.”
  • acid dyes is actually somewhat of a misnomer in that it does not describe any particular chemical type of dye, but rather refers to the traditional practice of dyeing fabrics from acidified solutions. Not all acid dyes are suitable for use in marker inks, however, and dyes having good chroma and color intensity and good water-solubility characteristics are typically utilized.
  • Marker inks ordinarily also include such ingredients as humectants, biocides, and surfactants.
  • Humectants function to improve freeze/thaw stability and to control drying out of the marker tip, while biocides serve the obvious function of preventing spoilage of the ink during the expected shelf life of the marker product.
  • a small amount of surfactant is ordinarily employed. It is important to note that surfactants, when used at all, are included in very low concentrations in marker inks in order to prevent the phenomenon known as "strike-through," where the ink soaks through the paper to which it is applied instead of remaining on the surface.
  • tints or dyes used in these "washable" markers are produced by the chemical grafting of a chromophore onto a water soluble polymer, such as polyethylene glycol, in an effort to impart improved fugitivity properties to the chromophore. While this approach is a workable one for enhancing fabric fugitivity, it is relatively expensive.
  • Another object is to provide a water-soluble dye-containing composition which, in addition to being washable from the skin, is more easily washable from fabrics.
  • a related object is to provide washable dye- containing compositions, such as paints and inks, which are suitable for use by young children who may make marks on themselves and their clothing.
  • Another related object is to impart skin fugitivity to dye-containing compositions without the necessity for chemical or other alteration of the dyestuff itself.
  • a further object is to impart skin fugitivity to dye-containing compositions which otherwise have good washability from textiles, but quite limited washability from skin.
  • the discovery of the present invention is that one may incorporate into a water-soluble dye-containing composition an additive which will impart to the composition fugitivity from skin. At the same time, it has been discovered that, in many instances, the additive will noticeably enhance fugitivity from fabrics ordinarily used in children's clothing. Thus, in accordance with the present invention, one may produce a water-soluble dye- containing composition which has unexpectedly good fugitivity from skin and, in many instances, enhanced fugitivity from textiles without the need for chemically altering the desired dye.
  • the discovery is that a material otherwise known for its dispersant properties, namely, an organic sulfonate, is effective to impart fugitivity from skin. And, as noted, this material may also enhance the fugitivity from fabrics of a dye- containing composition.
  • the discovery is that these unexpected results are achieved by the use of high concentrations of the organic sulfonate, inasmuch as such materials have traditionally been employed in rather low concentrations as dye dispersants and as tanning agents for leather.
  • the invention includes dye-containing compositions including an organic sulfonate which are easily washed from the skin, and, in addition, are also more easily washed from textiles.
  • the present invention includes a method of imparting skin fugitivity to a dye-containing composition by adding to the composition an effective amount of an organic sulfonate.
  • the invention is a washable dye-containing composition comprising a dye, a dye vehicle, and an organic sulfonate in an amount of at least about 10% by weight of the composition.
  • a washable dye-containing composition such as a marker ink, comprising a dye, water, and an aromatic sulfonate in an amount of at least about 10% by weight of the composition.
  • Such a marker ink which is especially suitable for use by children, also advantageously includes a humectant, a surfactant, and a preservative, all as are well known in the art.
  • the composition of the invention is in the form of a water- soluble tempera paint comprising a dye, water, fillers, thickeners, opacifiers, and an organic sulfonate in an amount of at least about 10% by weight of the composition.
  • the additive which has now been discovered to impart skin fugitivity and, in some instances, enhance fabric fugitivity of water-soluble dye-containing compositions when utilized in rather high concentrations; namely, an organic sulfonate, has long been used at low concentrations as a dispersant and as a tanning agent for leather.
  • All organic sulfonates are, in general, effective in the practice of the invention. Even lignin sulfonates are effective, though they tend to affect the color of the composition. In general, aromatic sulfonates are preferred for use in the marker ink compositions of the invention.
  • Alkyl sulfonates impart adequate fugitivity, but marker ink compositions which include them tend to produce the undesirable "strike-through" effect mentioned above, and they are therefore less preferred for such use.
  • those sulfonates which, in addition to imparting fugitivity from skin, also enhance fugitivity from textiles.
  • the sulfonates impart skin fugitivity and enhance fabric fugitivity is not known; however, it is believed that the sulfonates tie up the reactive site of the chromophore molecule, such that the chromophore has a reduced ability to physically or chemically associate with skin or fabric. It has been found, moreover, that simply sulfonating the dye molecule, much like grafting onto it a water soluble polymer, enhances water solubility, but confers no skin fugitivity.
  • Aristonate 430 sodium alkyl benzene sulfonate (Pilot Chemical Co.)
  • Aristonate 500 sodium alkyl benzene sulfonate (Pilot Chemical Co.) Blancol N sodium salt of sulfonated (GAF Corp.) naphthalene - formaldehyde condensate
  • Karasperse DDL sodium organic sulfonate (Lyndal Chemical Co.)
  • Karasperse DDL-12 modified sulfonate ( ynda1 Chemical Co.)
  • the beneficial effect of the organic sulfonate additive occurs when the additive is present at a concentration of at least about 10% by weight of the composition.
  • the weight ratio of additive to dye appears not to be critical.
  • the upper limit of the additive concentration is imposed only by the constraints on the viscosity of the composition in view of the fact that many organic sulfonates are solids. For example, a marker ink cannot have a significantly viscous consistency or it will not flow through a marker nib.
  • the maximum preferred concentration is about 25% by weight of the composition, since there is no observable benefit from higher concentrations.
  • compositions of the invention may, when in the form of a marker ink, also advantageously include a humectant, a surfactant, and a preservative.
  • a humectant in a marker ink to retard the evaporation of water from the ink solution.
  • a generally useful concentration range for these humectants is from about 5% up to about 30% by weight.
  • surfactant up to about 0.1% by weight
  • surfactant Small amounts of surfactant (up to about 0.1% by weight) are also useful in marker ink compositions for the purpose of adjusting such properties as viscosity (for proper dispensing of ink through the nib) , surface tension (for good flow properties without creating "strike- through'), and drying speed (for maximizing what is known as "cap-off" time; i.e., the length of time after which the nib of an uncapped marker will become clogged with dried ink).
  • Nonionic surfactants such as polyethylene glycol ether, alkylaryl polyether alcohol, fluorinated alkyl esters, and mixtures of such materials are preferred for use in marker inks.
  • Preservatives of conventional types are also advantageously employed in marker inks and tempera paints in order to extend the shelf life of the composition.
  • Some typical preservatives useful in the present invention include methyl p_-hydroxybenzoate, glutaraldehyde, and hydroxybenzoic acid esters. They are usually effective when present in an amount of from about 0.1% up to about 0.6% by weight.
  • the fugitivity from skin of the compositions of the invention was measured by the following test:
  • the fugitivity from fabric of the compositions of the invention was measured by the following test.
  • Skin fugitivity data are based on a visual rating system as follows:
  • the basic dyes used were as follows:
  • a black washable tempera paint was prepared by admixing the following, all amounts given in terms of weight per cent:
  • Tamol SN 10.91 biocide 1.23 calcium carbonate 33.60 talc 13.36 silica 4.11 hydroxymethyl 12.80 cellulose solution (2 1/2%)

Abstract

Dans un mode de réalisation, une composition contenant des colorants lavables comprend un colorant, un véhicule du colorant et une quantité de sulfonate organique égale à au moins 10 % en poids environ de la composition. Plus spécifiquement, dans un mode préférentiel de réalisation, une composition contenant des colorants lavables, tels que des encres à marquer, comprend un colorant, de l'eau et une quantité de sulfonate aromatique égale à au moins 10 % en poids environ de la composition. Dans un autre mode de réalisation, la composition se présente sous forme d'une détrempe qui comprend un colorant, de l'eau, des charges, des épaississeurs, des opacifiants et une quantité de sulfonate organique égale à au moins 10 % en poids environ de la composition. L'invention couvre d'autres compositions contenant des colorants solubles dans l'eau, y compris les peintures en pots souvent utilisées par les écoliers.
PCT/US1990/001939 1989-04-10 1990-04-10 Composition contenant des colorants lavables WO1990012067A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33527289A 1989-04-10 1989-04-10
US335,272 1989-04-10

Publications (1)

Publication Number Publication Date
WO1990012067A1 true WO1990012067A1 (fr) 1990-10-18

Family

ID=23311040

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/001939 WO1990012067A1 (fr) 1989-04-10 1990-04-10 Composition contenant des colorants lavables

Country Status (2)

Country Link
AU (1) AU5437890A (fr)
WO (1) WO1990012067A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998036031A1 (fr) * 1997-02-14 1998-08-20 Binney & Smith Inc. Composition colorante lavable utile dans des marqueurs effaçables a sec
WO1998036032A1 (fr) * 1997-02-14 1998-08-20 Binney & Smith Inc. Composition colorante lavable
US5981626A (en) * 1997-02-14 1999-11-09 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2396056A1 (fr) * 1977-06-30 1979-01-26 Pilot Ink Co Ltd Composition d'encre aqueuse pour instruments graphiques
EP0209367A1 (fr) * 1985-07-16 1987-01-21 Tosoh Corporation Composition d'encre pour tableau d'écriture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2396056A1 (fr) * 1977-06-30 1979-01-26 Pilot Ink Co Ltd Composition d'encre aqueuse pour instruments graphiques
EP0209367A1 (fr) * 1985-07-16 1987-01-21 Tosoh Corporation Composition d'encre pour tableau d'écriture

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998036031A1 (fr) * 1997-02-14 1998-08-20 Binney & Smith Inc. Composition colorante lavable utile dans des marqueurs effaçables a sec
WO1998036032A1 (fr) * 1997-02-14 1998-08-20 Binney & Smith Inc. Composition colorante lavable
US5900094A (en) * 1997-02-14 1999-05-04 Binney & Smith Inc. Image transfer method for use with water based dry erase markers
US5968241A (en) * 1997-02-14 1999-10-19 Binney & Smith Inc. Washable coloring composition
US5981626A (en) * 1997-02-14 1999-11-09 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
US6040359A (en) * 1997-02-14 2000-03-21 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
AU729526B2 (en) * 1997-02-14 2001-02-01 Binney & Smith Inc. Washable coloring composition suitable for use in dry erase markers
JP2001511839A (ja) * 1997-02-14 2001-08-14 ビニー アンド スミス インコーポレイティド 洗浄可能な着色組成物
KR100338693B1 (ko) * 1997-02-14 2002-05-30 안 드와이트 건식 소거（ｄｒｙ ｅｒａｓｅ）되는 마커에 사용적합한 세척 가능 착색 조성물

Also Published As

Publication number Publication date
AU5437890A (en) 1990-11-05

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