|||||||||||||| O US005378454A United States Patent (19) 11 Patent Number: 5,378,454 Burmeister 45) Date of Patent: Jan. 3, 1995 54 COMPOSITION AND PROCESS FOR 4,913,900 4/1990 Kolc ...................................... 424/72 PERMANENT WAVING 5,068,102 11/1991 Tennigkeit ............................ 424/72 (75) Inventor: Frederick H. Burmeister, Rumson, FOREIGN PATENT DOCUMENTS N.J. 40693A 11/1976 Germany .............................. 424/72 73)7 Assignee: Jo ha raPaul MitchellMi Systems, Santa Primary Examiner-D. Gabrielle Phelan Clarita, Calif. Assistant Examiner-Sally Gardner (21) Appl. No.: 819,085 Attorney, Agent, or Firm-Kalish & Gilster : s see ooooooooo-u an on ea o A6.9. £76g A waving lotion for use in an exothermic permanent Mve we sea as as a poo a no o vono so a use on 0 a was a ows 1327205 wave comprising an activator in an amount sufficient to - provide an exothermic reaction, with an effective perm 58) Field of Search ............................. 424/7, 2. ing amount of a reducing agent, wherein the reducing agent is a combination of a more active reducing agent (56) References Cited and a less active reducing agent in a ratio necessary to U.S. PATENT DOCUMENTS effect a reduction in hair damage, wherein the less 2C 3,768,490 10/1973 Kalopissis 424/72 tive reducing agent is an ester of thioglycolic acid. 4,134,411 1/1979 Yamazaki .............................. 424/72 4,158,704 5/1979 Baer .................................... 132/204 2 Claims, No Drawings 5,378,454 1. 2 COMPOSITION AND PROCESS FOR KSSK--2 RSH-2 KSH--RSSR PERMANIENT WAVING The reduced keratin is rebonded with the hair in a THE FIELD OF THE INVENTION 5 curled configuration to effect a permanent set. This The present invention relates to the permanent wav rebonding is accomplished by the action of a chemical ing of hair. It particularly relates to a waving lotion and oxidation agent, commonly referred to as the perma a process for using it in exothermic permanent waving. nent wave neutralizer. Typically, the oxidizing agents The permanent wave lotion of the present invention used in most neutralizers are hyrodgen peroxide and comprises an activator and a reducing agent containing 10 sodium bromate. The chemical oxidation (neutraliza a combination of a more active reducing agent and a less tion) reaction is illustrated in the following reaction: active reducing agent, wherein the less active reducing 2 KSH--O-KSSK--H2O agent is an ester of thioglycolic acid. When the activa tor and the reducing agent are combined in the appro S The exothermic reaction of the present invention is priate proportions, an exothermic permanent wave is illustrated in the following reaction: produced. BACKGROUND OF THE INVENTION 2 RSH--H2O2 -RSSR-2H2O--heat The activity or effectiveness of hair shaping prepara The di-thio formed acts to form a reverse equilibrium tions is based mainly on the inclusion therein of an agent reaction which serves to significantly slow the reduc for softening and relaxing the keratin protein present in tion of the keratin to effect a "stop action' of the perma hair by reducing the disulfide (S-S) linkages of keratin nent waving process. This provides better control of the which covalently link adjacent polypeptide chains (K). perming effect. The hair fiber is wound on rods to achieve the desired U.S. Pat. No. patent 4,793,994 discloses a cold wave waving effect or manipulated into a straightened condi 25 permanent wherein a N-alkyl lactam is incorporated tion and allowed to remain wetted with the reducing into a hair perming lotion. One of the effects of the lotion for a desired period, after which the reducing addition of the lactam is a conditioning effect on the lotion is rinsed off and finally oxidized with a neutraliz hair. The permanent wave composition contains a wav ing solution or air oxidized. 30 ing solution, which is a reducing solution that can con Basically, hair is softened and swelled by the use of a tain ammonium thioglycolate (ATG) and/or glyceryl mild alkaline reducing agent. Cleavage of at least some monothioglycolate (GMT). GMT is known to be a less of the disulfide bonding to form the corresponding active reducing agent and is suitable for bleached, cystine residue is necessary to allow for molecular rear permed or damaged hair. The permanent wave compo rangement which takes place during the hair fiber mold 35 sition contains a neutralizing solution containing hydro ing operation. The reductive fission of hair disulfides gen peroxide. This lactam may be used in cold or hot generally causes reddening of the scalp area and dam WaVeS. - age to the hair fiber, particularly hair which has been U.S. Pat. No. 4,158,704 discloses a method of perma bleached, tinted or otherwise damaged. Current hair nent waving which eliminates the subjective judgment structure altering lotions which provide relaxation of 40 of the operator in determining the conditions for wav imposed stress include aqueous solutions of alkaline ing. This method is used with cold or hot waves, mercapto compounds, sulfites or bisulfites at a pH of wherein the waving lotion is a reducing lotion which between 4 and 10. In order to obtain a permanent effect, may contain AGT and/or GMT. A neutralizing solu particularly in hair straightening, it is often necessary to tion is used containing an oxidizing agent, such as per introduce the active agent in relatively high concentra 45 oxide. The method involves a numerical rating the con tions with the result that the reducing lotion is provided centration of the waving solution, the pH of the solu at almost the limit of its physiological compatibility or tion, the condition of the hair and the porosity of the tolerability. hair. Based on an evaluation of the above four parame Damage to hair is increased where heat waving, as ters, the time and the temperature of the perm is deter opposed to cold waving, is employed. Of the reducing 50 mined. agents currently in use, the thioglycolates or thiogly U.S. Pat. No. 4,963,349 discloses a permanent wave colic acid, dithioglycolic acid and mercapto compounds solution employing a 1,3-alkyldiol in its reducing solu such as ammonium thioglycolate, glyceryl monothio tion. The alcohol solution provides a permanent wave glycolate, mercaptopropionic acid and mercaptoethyl solution employing ATG at a pH in the same acidic amine are most often employed in the professional wav 55 range as the isoelectric point of hair (pH3 to 5), or a five ing or hair straightening of the present invention. In lieu minute permanent wave with either an acid or alkaline of the heat waving or cold waving, the oxidizing wav solution. The use of GMT is discouraged as an "expen ing of the present invention can be effected by oxidizing sive chemical which must be packaged separately.” The the mercaptain with an agent, such as hydrogen perox perms are hot or cold waves. ide, an iodate or a bromate. This oxidizing solution is 60 U.S. Pat. No. 4,273,143 discloses a permanent wave typically called an activator. solution that can be used in conjunction with an exo The reducing agent used in exothermic perms is typi thermic wave, having a waving lotion suitable for si cally a mercaptan (RSH), such as ammnonium thiogly multaneous use on both bleached and unbleached hair colate (ATG). The chemistry involved in the reaction containing a lipoidal alkyl chain having ten or more of a mercaptan with the cystine disulfide bonds (KSSK) 65 carbon atoms and a disulfide derivative of a mercaptan in the hair fiberto foden a disulfide, such as dithioglyco with a substituent group. The preferred compounds late and a keratin residue is illustrated by the following contain a quaternary ammonium group and a dithio chemical equation: derivative of a thioglycolate. 5,378,454 3 4. None of the above references disclose the present 8.5 to 9.5. At a pH lower than 8.5, the effectiveness of permanent wave solution for exothermic permanent waving is reduced as the rate of reduction is decreased. waving. At a pH higher than 9.5, irritation of the scalp may occur, and the stop action effect will diminish. THE PRESENT INVENTION The reducing lotion is generally employed with an The present invention is a waving lotion for use in alkali having a dissociation constant less than 5X10-3. exothermic permanent waving comprising an activator Suitable compounds for alkalization include ammnonia, in an amount sufficient to provide an exothermic reac ammonium hydroxide, sodium hydroxide, ethanol tion with an effective perming amount of a reducing amine, diisopropanolamine and an alkalimetal salt of an agent wherein the reducing agent contains a combina 10 amino acid, e.g. glycine, lysine or guanidine. Alkali in a tion of a more active reducing agent and a less active concentration of between about 0.5 and about 10.0% is reducing agent in a ratio necessary to effect a reduction normally used. in hair damage, wherein the less active reducing agent is Other additives which may be employed include an ester of thioglycolic acid. catalysts for self-neutralizing permanent wave lotions, 15 opacifiers to promote creamy appearance and fragrance DETALED DESCRIPTION OF THE PRESENT to mask the odor of ammnonia and thiol. A native pro INVENTION tein such as a soluble glycoprotein, or a hydrolysed The permanent waving lotion of the present inven protein, may also be added to the reducing lotion to tion comprises an activator, a more active reducing moisturize and condition the hair. A preferred glyco agent and a less active reducing agent. The activator 20 protein is Glyprosol 20, a registered trademark of causes an exothermic reaction to be effected when the Brooks Industries, Inc., having a molecular weight of activator is mixed with the waving lotion by oxidizing about 10,000, a protein content of about 10% and an the mercaptain with an oxidizing agent, such as hydro oligosaccharide content of about 8%.