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US 20090324846A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0324846A1 Tomaschke et al. (43) Pub. Date: Dec. 31, 2009 (54) POLYENE PIGMENT COMPOSITIONS FOR Publication Classification TEMPORARY HIGHILIGHTING AND (51) Int. Cl MARKING OF PRINTED MATTER C09D II/02 (2006.01) (75) Inventors: John Tomaschke, San Diego, CA C08. 7/8 (2006.01) S. George Brown, Ramona, CA (s2 usic... 427/553; 106/31.6 Correspondence Address: (57) ABSTRACT BioTechnology Law Group 12707 High Bluff Drive Disclosed herein are compositions comprising a polyene Suite 200 compound and an additive selected from the group consisting fantioxidant. Surfactant, oil. wax. Solvent, and a combina Sanan DDiego, CA92130-2037 (US)US tionO thereof. Alsos discloseds Yu herein us ares methodss oftemporarily (73) Assignee: B&T TECHNOLOGIES, LLC marking a surface comprising marking the Surface with a San Diego, CA (US) s composition as disclosed herein, where the marking has a s color intensity; and exposing the Surface to ambient light and (21) Appl. No.: 12/146,400 ambient air, whereby the color intensity of the marking decreases over a period of time. Further, disclosed herein are (22) Filed: Jun. 25, 2008 markers comprising a composition as disclosed herein. US 2009/0324846 A1 Dec. 31, 2009 POLYENE PIGMENT COMPOSITIONS FOR soluble crayon markings on paper result in unsatisfactory TEMPORARY HIGHILIGHTING AND wrinkling damage of the paper Substrate. All of the aforemen MARKING OF PRINTED MATTER tioned color highlighting or marking removal techniques for paper Substrates require a time consuming additional treat FIELD OF THE INVENTION ment step. In particular, this additional removal step is very impractical for the quantities of textbook highlighting accu 0001. The present invention relates to the temporary high mulated during School sessions lasting from one to nine lighting of printed matter with liquid or Solid highlighting months. compositions containing polyene pigments. These non-toxic 0011 Clearly, the need exists for a means of highlighting pigments may be obtained from either natural sources or or marking textbooks and other printed matter Such that this synthetic equivalents and are safe for use by School children. highlighting or marking disappears over controllable time periods without the need for additional dangerous or time BACKGROUND OF THE DISCLOSURE consuming treatments. 0002 U.S. Pat. No. 5,055.498 relates to erasable crayons fabricated from Solid marking compositions incorporating SUMMARY OF THE INVENTION polyethylene resins. 0012 Disclosed herein are compositions comprising a 0003 International Patent WO/1993/024580 features polyene compound and an additive selected from the group erasable marking compositions in Solid form which can be consisting of antioxidant, Surfactant, oil, wax, solvent, and a applied to and erased from paper Substrates. One aspect of combination thereof. In some embodiments, the polyene this invention includes a solid erasable highlighting compo compound is a carotenoid polyene. In certain embodiments, sition containing a block copolymer, wax, and fluorescent the polyene compound is selected from the group consisting pigment. of antheraxanthin, astacin, astaxanthin, canthaxanthin, cap 0004 International Patent WO/1995/004785 relates to Santhin, carotenes, cryptoxanthin, diatoxanthin, didehy water soluble crayon composition comprising ethoxylated droastaxanthin, echinone, lutein, lycopene, lycophyll, lycox anthin, rhodopin, rhodoviolascin, rhodoxanthin, rubiXanthin, alcohol, a pigment or dye, and a filler material. Markings onto spheroidene, spheroidenone, spirilloxanthin, and their sac various surfaces are removable by water. charide derivatives. Some of the polyene compounds dis 0005 U.S. Pat. No. 5.453,120 describes erasable fluores closed herein are naturally occurring polyene compounds, cent marking materials and markers made therefrom in which whereas others are synthetic polyene compounds. a wax-based vehicle contains a suspension of fluorescent 0013. In some embodiments, the antioxidant is selected pigment particles. from the group consisting of BHT (2,6-bis 1,1-dimethyl 0006 International Patent WO/1985/0007782 and its ethyl-4-methylphenol), ascorbyl palmitate, and the like. counterpart U.S. Pat. No. 4,681,471 relate to kits of colored 0014. In some embodiments, the oil is vegetable oil. fluid marking devices in combination with means for eradi 0015. In certain embodiments, the wax is selected from the cation of the marks. An example is arylmethane-based color group consisting of candle wax, paraffin Fischer Tropsche ing marks eradicated with sodium metabisulfite reducing wax, carnauba wax, paraflint wax, and the like, and combi agent from a variety of Surfaces. nations thereof. 0007 U.S. Pat. No. 5,362,167 features aqueous-based 0016. In some embodiments, the solvent is an aqueous erasable marking compositions containing a latex emulsion Solvent. In certain embodiments, the solvent is a combination and a water insoluble pigment. Included are highlighters for of water and an organic solvent. In further embodiments, the paper Substrates. organic solvent is an alcohol. 0008 International Patent WO/1996/039302 and its coun 0017. In some embodiments, the compositions disclosed terpart U.S. Pat. No. 6,066.439 describe temporary marking herein further comprise a Sublimable organic compound, and printing of various Surfaces where a photoerasable colo which may include a compound selected from the group rant composition is employed. The photoerasable colorant consisting of camphene, camphor, p-dichlorobenzene, p-hy composition comprises a mutable colorant and an ultraviolet droxybenzaldehyde, quininone, quinuclidine, and trioxane, radiation transorber. Ultraviolet light irradiation renders the and the like. colored marking colorless. 0018. Also disclosed herein are methods of temporarily 0009 U.S. Pat. Nos. 5,324,131 and 5,427,278 relate to marking a surface comprising marking the Surface with a method and apparatus, respectively, for removing water composition of as disclosed herein, where the marking has a based, non-pigmented highlighting markings from a paper color intensity; and exposing the Surface to ambient light and Surface. The color removing agents consist of bleaches and ambient air, whereby the color intensity of the marking other oxidizing chemicals. decreases over a period of time. In some embodiments, the 0010. There are thus three basic approaches in the prior art marking disappears over a period of time, which can be a for removing colored highlighting or marking on printed period of months or a period of hours. paper Substrates: physical contact (rubber eraser), chemical 0019. Further, disclosed herein are markers comprising a treatment, and ultraviolet light irradiation. Each of these tech composition as disclosed herein. In some embodiments, the niques suffers from one or more disadvantages. Erasure, marker is a crayon, whereas in other embodiments, the when done repeatedly, erodes the surface of printed matter marker is a highlighter. In some embodiments, the marker including the printing ink which resides therein. Chemical further comprises a wick. treatment involves use of toxic, corrosive, or irritating com pounds which would be unsafe for children. Ultraviolet light DETAILED DESCRIPTION OF THE irradiation carries with it the risk of eye injury as well as EMBODIMENTS complexity and would also be unsuitable for children. It 0020. In one aspect, disclosed herein are colored compo should be further mentioned that using water to remove water sitions that lose their color over a period of time, highlighter US 2009/0324846 A1 Dec. 31, 2009 pens and devices that use these compositions, and methods of compounds' even though they were synthesized from labo making and using the highlighter pens and devices. In some ratory reagents and commercially available precursors. A embodiments, disclosed herein are compositions comprising “synthetic polyene compound is a compound that is synthe a polyene compound and an additive selected from the group sized in a laboratory and is not structurally identical to a consisting of antioxidant, Surfactant, oil, wax, solvent, and a naturally occurring compound. Some synthetic polyenes are combination thereof. derivatives of naturally occurring polyenes. Derivatives are 0021. In some embodiments, the polyene compound is a obtained by methods known to those of skill in the art, for carotenoid polyene. In some embodiments, carotenoid poly example, by adding a protecting group, removing a substitu enes, which are found widely distributed in nature, are used in ent, adding a new Substituent, and the like. the compositions disclosed herein. Carotenoids are defined by their chemical structure. The majority carotenoids are 0026. It has now been discovered that carotenoid pigment derived from a 40-carbon polyene chain, which could be coloring on printed paper Substrates, such as a textbooks, used considered the backbone of the molecule. A “polyene chain' in a typical indoor environment can be made to disappear is a chain of carbon atoms comprising repeating single and controllably timewise through the selection of a proper caro double bonds. In some embodiments, a polyene chain com tenoid compound. While not bound by any particular theory, prises a chain of the following repeating unit. —CH2— it is postulated that the longer the conjugated double bond CH=CH-. In some embodiments, the polyene compound backbone is, the more rapid is its oxidative degradation
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