USOO8414872B2 (12) United States Patent (10) Patent No.: US 8,414.872 B2 Resnick et al. (45) Date of Patent: Apr. 9, 2013 (54) HAIR STRAIGHTENING FORMULATIONS, 6,602,493 B2 8, 2003 Akhter METHODS AND SYSTEMS 6,610,280 B2 8/2003 Ainger 6,696,067 B2 2/2004 Brandt 6,709,648 B2 * 3/2004 Sako et al. ................. 424.70.12 (75) Inventors: Lionel Resnick, Weston, FL (US); Irwin 6,805,136 B2 10/2004 Browning Grams, Boca Raton, FL (US); Angela 6,994,846 B2 2/2006 L'Alloret Goodfellow, Ottawa (CA); David Alice, 7,025,955 B2 4/2006 Siddiqui 7,105,184 B2 9/2006 Pauly Toronto (CA) 7,148,327 B2 12/2006 Kelly 7,250,174 B2 7, 2007 Lee (73) Assignee: Liquid Keratin, Inc., Ottawa (CA) 7,318,929 B2 1/2008 Schieferstein 7,390,468 B2 6/2008 Pekkala (*) Notice: Subject to any disclaimer, the term of this 7,390.478 B2 6/2008 Akyuz patent is extended or adjusted under 35 7,867.478 B2 * 1/2011 Nicolas-Morgantini U.S.C. 154(b) by 963 days. et al. ............................ 424,702 2002/0182161 A1 12/2002 Ainger 2003,0003070 A1 1/2003 Eggers (21) Appl. No.: 12/206,374 2003/0235554 A1 12/2003 Chahal 2004/0052748 A1 3/2004 Vondruska (22) Filed: Sep. 8, 2008 2004/O10583.6 A1 6/2004 Seipel 2005, 0186164 A1 8/2005 Akyuz (65) Prior Publication Data 2005/02O1967 A1 9, 2005 Albrecht 2006/0057090 A1 3/2006 Buchwald-Werner US 2009/O165812 A1 Jul. 2, 2009 2006, O104928 A1 5, 2006 Furtado 2006, O165635 A1 7/2006 Kelly 2006,0183662 A1 8/2006 Crotty Related U.S. Application Data 2006, O19476.0 A1 8, 2006 Griesbach (60) Provisional application No. 60/971,001, filed on Sep. 2006, O251602 A1 11/2006 Goddinger 2007/0048235 A1 3/2007 Harmalker 10, 2007. 2007/O185281 A1 8/2007 Song 2007/0202069 A1 8/2007 Tamaeselvy (51) Int. Cl. 2007/0207097 A1 9/2007 Kelly A61O5/04 (2006.01) 2008.0004423 A1 1/2008 Kelly (52) U.S. Cl. ....................................... 424/70.2; 132/202 FOREIGN PATENT DOCUMENTS (58) Field of Classification Search ........................ None DE 102004.002168 A1 8, 2005 See application file for complete search history. WO WO2007032762 3, 2007 (56) References Cited * cited by examiner U.S. PATENT DOCUMENTS Primary Examiner — Jyothsna Venkat 4,148,329 A 4, 1979 Jaskowski (74) Attorney, Agent, or Firm — Cowan, Liebowitz & 4,304.244. A 12, 1981 de la Guardia Latman, P.C. 4,591497 A 5, 1986 Naito 4,806,595 A 2f1989 Noishiki (57) ABSTRACT 4,898,726 A 2f1990 Beste 4,911,919 A 3, 1990 Patel The present invention includes a hair straightening formula 5,080,670 A 1/1992 Imamura tion consisting of a hair fixative that will straighten the hair for 5,639,449 A 6/1997 Syed at least 2-3 months after one application despite frequent 5,641,478 A 6/1997 Syed 5,679,327 A 10, 1997 Darkwa washings of the hair as well as methods for obtaining said 5,753,214 A 5, 1998 Yoshioka formulation. The formulation comprises as active ingredients 6,007,585 A * 12/1999 Syed et al. ........................ 8.432 one or more keratin hydrolysates and an aldehyde. Hair 6,284.230 B1 9, 2001 Sako straightening system comprising shampoo and one or more 6,306,805 B1 * 10/2001 Bratescu et al. .............. 510,123 6,376.455 B1 4/2002 Friedli conditioners are also provided. The invention is further 6,491.933 B2 12/2002 Lorenzi directed to a method for straightening hair using said formu 6,494,920 B1 12/2002 Weuthen lation. 6,555,505 B1 4/2003 King 6,596,035 B2 7/2003 Gutkowski 4 Claims, No Drawings US 8,414,872 B2 1. 2 HAIR STRAIGHTENING FORMULATIONS, ingredients: (a) one or more keratin cross-linking agents and METHODS AND SYSTEMS (b) one or more keratin protein fractions. In a particular embodiment, the keratin cross-linking agent comprises a PRIORITY CLAIM nonformaldehyde aldehyde, more particularly a dialdehyde This application claims the benefit of provisional applica and even more particularly, glyoxal. The hair straightening tion Ser. No. 60/971,001, filed Sep. 10, 2007 under 35 USC formulations may be in the form oflotion, cream, gel, spray, 119(e), the contents of which are incorporated herein by foam, ointment, shampoo, conditioner, aerosol, mousse or reference. liquid Suspension in a sponge or other applicator. In certain advantageous embodiments, the hair straighten FIELD 10 ing formulations are guanidinium, formaldehyde, paraben and lye free. In a specific embodiment, the hair straightening One or more hair straightening formulations are provided formulations comprise (a) one or more dialdehydes; (b) one to straighten the hair for at least 2-3 months after one appli or more keratin protein fractions and optionally (c) at least cation despite frequent washings of the hair. One or more hair straightening systems comprising said formulation as well as 15 one of (i) one or more surfactants; (ii) one or more emollients; one or more shampoos and one or more conditioners are (iii) one or more emulsifiers; (iv) one or more preservatives, provided. In addition, one or more methods for straightening (v) one or more skin protecting agents and (v) one or more hair using said formulations and systems are provided. diluents. In a particular embodiment, the formulations comprise BACKGROUND each of the components in the following amounts: Human hair has many textures, from fine to coarse and from straight to curly. Hair is made of keratin which in turn is made of polypeptide chains bonded together by cysteine (or Substance % By Weight disulfide) bonds, hydrogen bonds and salt linkages. 25 Dialdehyde O.OS-10% Curly hair is made of hair strands that have irregular sur Keratin O.OS-15% faces that mesh and tangle with each other to make combing Surfactant O.1-15% more difficult. Among individuals with very curly hair, e.g., Emollient O.1-15% individuals of African or Middle Eastern descent, it is espe Emulsifier O.1-15% cially popular to relax or straighten hair to increase hair Preservative O. 1-5% 30 Diluent O. 1-5% manageability and ease of Styling. Threads are composed of Skin protecting agent O.1-10% proteins of spiral structures, linked by a sulfur double-bond. These bonds are responsible for the hair structure and they may be broken by certain reduction reactions. The most com The formulations may also comprise one or more thickeners, mon reductive agents are thioglycolic acid and its derivatives fragrances and/or Sunscreen agents. Such as ammonium thioglycolate and bisulfite. These act on 35 In yet a more specific embodiment, the hair straightening the hair keratin by breaking disulfide bonds that link cysteine formulations comprise glyoxal, hydrolyzed keratin, one or units; this way, they form cysteine, the main component of more silicone containing emollients, one or more polyoxy keratin. The hair to be relaxed is exposed to a relaxer that ethers of lauryl alcohol, one or more glycerin compounds, chemically transforms cysteine bonds of the hair to lanthion one or more skin cleansing agents, phenoxyethanol and an ine bonds. For this reason, the term for the chemical relaxing 40 aqueous based diluent. process is lanthionization. In yet another embodiment, the hair straightening formu Hair straightening or hair relaxing products have been lations provides a gelatinous aqueous thermal hair straight commercially available for over forty years for people who ening and conditioning formulations that preferably impart a want straighter and more manageable hair. Most commer firm and silky look and feel to hair and inhibits wind and cially available hair relaxers are composed of a strong 45 motion induced hair scattering during use. The formulations hydroxide base that breaks the bonds in the hair. The first comprise glyoxal, amino acids of hair keratin, epigallocat straightening chemicals were developed around 1940. They echin gallate, water, propylene glycol, cetearyl alcohol, ceta were rudimental preparations of Sodium or potassium rimonium chloride, amondimethicone, cyclopentasiloxane, hydroxide blended with starch and they were highly irritating dimethicone and fragrance. The hair straightener and condi to the scalp. By the 1950s, several kits for chemical straight 50 tioner formulations preferably are used before hot iron ening, based on Sodium hydroxide, were introduced in the straightening of curly hair, and imparts a Smooth and silky professional market. In 1965, the market already had a chemi feel to hair. cal straightening product for home use, based on Sulfites. In Also provided are uses of these hair formulations set forth 1985, Avon Industries introduced a straightening system above in Straighteninghair. Specifically, methods for straight based on types of hair and Scalp sensitivity (i.e., normal and 55 ening hair are provided comprising applying an amount of sensitive). The first one used sodium hydroxide as its active these formulations and for a time effective to straighten hair. ingredient and the other used guanidine hydroxide. However, Further provided are one or more hair straightening sys the results provided by existing straightening products are not tems comprising (a) the hair straightening formulations set optimal; nor is their safety. Current products present incon forth above; (b) one or more shampoos and (c) one or more Venience issues, such as weakening of threads, irritation of 60 conditioners. the scalp and difficulty in rinsing. Also due to their instability, The term "modulates hair frizz' and "defrizzes hair are these formulations degrade rapidly. used interchangeably. Inaparticular embodiment, at least one of the shampoos and/or at least one of the conditioners modu SUMMARY lates hair frizz. As defined herein “modulates' means that it 65 either reduces or prevents hair frizz.