United States Patent (19) 11 4,301,046 Schlossman 45} Nov. 17, 1981 54 UNIVERSAL NAIL POLISH USING POLYESTER RESN FOREIGN PATENT DOCUMENTS 41-1 1000 6/1966 Japan ..................................... 424/61 75 Inventor: Mitchell L. Schlossman, Rockaway, N.J. Primary Examiner-Maurice J. Welsh Assistant Examiner-N. M. Nutter 73) Assignee: Tevco Inc. Attorney, Agent, or Firm-Toren, McGeady & Stanger 57 ABSTRACT 21 Appl. No.: 111,174 A nail polish is made from 92% to 96% ingredients including a film former, colorant, plasticizer and sol 22 Filed: Jan, 10, 1980 vent; and 4% to 8% polyester resin made from 2,2,4- trimethyl-1,3-pentanediol, isophthalic acid-85, and tri 51) Int. Cl. ................................................ C08L 1/10 mellitic anhydride, having an acid value of 75-85 and a 52) ... 260/16; 424/61 viscosity of 125-175 centipoise. In another example, the 58) Field of Search ............................. 260/16; 424/61 polyester is made from 50.932%. 2,2,4 trimethyl-1,3- pentanediol, 27.579% isophthalic acid-85, 0.186% dibu 56) References Cited tyl tin oxide catalyst and 21.303 trimellitic anhydride, U.S. PATENT DOCUMENTS having an acid value of 80 and a viscosity of 150 centi 2,215,898 9/1940 Anderson .............................. 424/61 poise, 3,849,547 11/1974 Kalopissis ....... ww. 424/61 4,022,724 5/1977 Kreuder et al. ... 260/16 29 Claims, No Drawings 4,301,046 2 tricresyl phosphate (24-255 C.), triphenyl phosphate UNIVERSAL NAL POLESH USENG EPOLYESTER and citrate piasticizers. RESN Colorants for nail enamel are usually confined to the non-bleeding in lacquer solvents. The most widely used BACKGROUND OF THE INVENTION 5 pigments in opaque enamels are red organic pigments, This invention relates to nail polishes, and particu D & C Red #6, #7, #9, #10, #30, #33, and #34 Lakes, arly, to hypo-allergenic nail polishes. D & C Yellow if5 Lakes, titanium dioxide, iron oxides The chief requirements of a satisfactory nail enamel used to produce brown and tan shades and iron black are that it should apply easily, be well adherent, dry and and iron blue. Basic Violet # 1 and #3, D & C Red #17, harden quickly, be glossy, waterproof and suitably col 10 D & C Violet #2 and D & C Red #19 dyes are the most ored, wear well, be elastic, resist chipping, peeling and widely used soluble dyes for transparent systems. Pig abrasion for a reasonable period of time, and be der ments with relatively high specific gravities such as matologically innocuous. titanium dioxide and the iron oxides are most widely In general, the main constituents of a nail enamel are used in "creme' shades and most responsible for pig the film former, a resin, colorants, plasticizer and sol S ment settling problems. Verits. An example of one formulation in percentages by Nail lacquer formulations have depended on nitrocel weight of the total composition (w/w%) is: lulose as its main film-forming ingredient for many years. Derived from cellulose, it provides an unusual combination of properties of toughness, durability, solu 20 W/W 2. bility, and solvent release. Nitrocellulose RS. sec.(dry) 15.00 film former Santolite resin (1) 12.00 resin Nitrocellulose must be neutral, for free acid could Dibutyl phthalate 3.00 plasticizer damage the fingernail and destroy the colors of the Butyl Acetate 31.50 solvent polish. The most commonly used viscosity grades of Ethyl Acetate 9.00 solvent (to speed dry) nitrocellulose are so-called RS sec., which has a high 25 Ethyl Alcohol 6.40 diluent-(coupling agent) solids content, but poor wear resistance, RS sec., Butyl Alcohol 1.10 diluent-(coupling agent) which has better wear resistance and a reasonably high Toluene 2.00 diluent non-volatile content, and lastly, RS 5-6 sec. and RS Colorant .00 60-80 sec., which have higher viscosities than the RS 100.00 Sec. grade. s 30 The term RS refers to the RS brand of nitrocellulose Reports of allergy due to nail polish usage have been with a nitrogen content of 11.2-12.8% with solubility in documented and attributed to the sensitization effects of esters, ketones and glycol ethers manufactured by Her resins such as the arylsulfonamide/formaldehyde resins. cules, Inc. The terms sec., 3 sec., 5-6 sec., etc. repre Attempts have been made to overcome this defi sent viscosity and refer to the time it takes for a ball to 35 ciency by substituting natural resins and polyesters as fall to a given depth in the material. nitrocellulose modifiers in the manufacture of nail pol Nitrocellulose is supplied in 70% concentrations, wet ishes. However, the result has been nail enamels having with 30% ethyl or isopropyl alcohol. Fingernail polish poor gloss and adhesion. grade nitrocellulose has a low moisture content. Resins An object of the present invention is to overcome are used in nitrocellulose compositions to improve their these disadvantages. depth, gloss and adhesion. The most widely used modi Another object of the invention is to produce hypo fying resin in nail enamel is the toluenesulfonamide/for allergenic nail polishes approximating the quality and maldehyde resin which provides excellent depth, gloss, characteristics of ordinary nail polishes. fiow and adhesion as well as good resistant films. Addi Still another object of this invention is to produce a tion of this resin and others permits an increase in solids 45 superior nail polish which is hypo-allergenic and can content without appreciably increasing lacquer viscos thus be utilized as a universal nail polish. ity. Nail enamels, using a minimum of coats, are more easily attained. SUMMARY OF THE INVENTION The solvent combinations used in nail lacquer tech According to a feature of the invention, a nail polish nology usually consists of the alcohol which is used to 50 is made from 92 to 96% film former, colorant, plasti wet the nitrocellulose, together with an active solvent cizer and solvent ingredients; and 4 to 8% polyester such as butyl acetate and an aromatic hydrocarbon resin. All percentages cited herein are percent by diluent such as toluene. Additionally, solvents used are weight of the total composition unless otherwise speci diluents. Diluents are organic solvents that are miscible fied. with the nitrocellulose solvents, but are not themselves 55 According to another feature of the invention, the solvents for nitrocellulose. They are used to reduce the polyester resin is a reaction product of 2,2,4-trimethyl-1, cost of formulation and help to lower and stabilize the 3-pentanediol, isophthalic acid-85, and trimellitic anhy viscosity of the enamels. Alcohols, aromatic hydrocar dride, and a catalyst. bons and aliphatic hydrocarbons are the classes of dilu According to another feature of the invention, the ents used. Ethyl (78 C.), isopropyl (82.3 C.), and butyl 60 polyester resin used is a synthetic hard water-reducible alcohol (118' C.) are the most efficient. "polyester resin' which is the reaction product of Most modern nail enamel formulations use a combi (40%-60%) 2,2,4-trimethyl-1,3-pentanediol, (22-33%) nation of camphor and another plasticizer. No one plas isophthalic acid-85, and (16%-26%) trimellitic anhy ticizer possesses all the desirable properties necessary to dride, and an 0.1 to 0.3% dibutyl tin oxide catalyst obtain permanent extensibility and flexibility in the re 65 having an acid value of 75 to 85, preferably 78-82, and sulting films. Commonly used solvent-type plasticizers most preferably 80. The term acid value is the value are dibutyl phthalate (bp 340 C.), dioctyl phthalate, determined by finding how many miligrams of KOH diphenyl phthalate, camphor, dibutoxyethyl phthalate, are needed to neutralize 1 gram of the resin (according 4,301,046 3 4. to American Oil Chemists Society standard test from 80, the lacquer becomes less viscous but remains CD3A63 set forth in Official and Tentative Methods of acceptable until it falls outside the 75 to 85 range. the American Oil Chemists Society, Second Edition, As used in this application, the acid value is the including additions and revisions, 1947-1963. amount of unreacted acidity in the resin as measured by More specifically, according to a feature of the inven- 5 the number of milligrams of KOH needed to neutralize tion, the synthetic hard water-reducible "polyester 1 gram of the polyester resin. The acid value is mea resin' is made from (50.932%) 2,2,4-trimethyl-1,3-pen sured by American Oil Chemists Society Test CD3A63, tanediol, (27.579%) isophthalic Acid-85, (21.303%) in Official and Tentative Methods of the American Oil trimellitic anhydride, and (0.186%) dibutyl tin oxide Chemists Society, Second Edition, including Additions catalyst, heated at 204' C. to obtain an acid value of 10 and Revisions, 1947-1963 inclusive. 75-85, preferably 75-82, and most preferably 80. The procedure for forming the polyester resin is as According to another feature of the invention, the follows: charge the 2,2,4-trimethyl-1,3-pentanediol and polyester resin is dissolved in a solvent to a viscosity of the isophthalic acid-85 in a kettle and heat to melt. 150 centipoise as determined using a model LVF Begin agitation, equip kettle for reflux processing at Brookfield Viscometer at 77 with a #3 spindle at 20 15 104 C. Charge dibutyl tin oxide catalyst and continue rpm. Preferably, the solvent is butyl acetate. heating to 204 C. over a two to two and one half hour According to another feature of the invention, part of period, then return the decomposition product to the the ingredients utilize a solid acrylic copolymer as an kettle. Hold for an acid value of 6 to 8.