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United States Patent (19) 11) 4,192,863 Kondo (45) Mar

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United States Patent (19) 11) 4,192,863 Kondo (45) Mar United States Patent (19) 11) 4,192,863 Kondo (45) Mar. 11, 1980 54 COMPLETELY ONE-STEP PERMANENT 56) References Cited WAVESOLUTION AND AMETHOD FOR U.S. PATENT DOCUMENTS USING THE SAME 2,631,965 3/1953 Schnell ................................... 424/72 (76 Inventor: Tokuzo Kondo, 92, Nishi-Koiso, 3,025,218 3/1962 Strain et al.. ... 424/72 Ohisomachi, Kanagawa Prefecture, 3,148,126 9/1964 Martin .................................... 424/72 Japan FOREIGN PATENT DOCUMENTS (21) Appl. No.: 587,623 36-299121 1/1961 Japan ......................................... 424/72 (22 Filed: Jun. 17, 1975 OTHER PUBLICATIONS Chem. Abstracts, vol. 56 (1962), 6106(c). Related U.S. Application Data Primary Examiner-Frederick E. Waddell 63 Continuation-in-part of Ser. No. 363,735, May 24, Attorney, Agent, or Firm-Haseltine, Lake & Waters 1973, abandoned, which is a continuation-in-part of Ser. No. 735,203, Jun. 7, 1968, abandoned, which is a 57 ABSTRACT continuation-in-part of Ser. No. 459,879, May 28, 1965, A completely one-step permanent wave solution which abandoned, which is a continuation-in-part of Ser. No. is harmless and effective on hair to provide odorless, 80,758, Jan. 5, 1961, abandoned. non-porous and silky and intrinsic permanent wave hair (30) Foreign Application Priority Data and consisting of ammonium thioglycolate, oxy-organic acid, ethyl alcohol, caustic alkali, ammonia water, or Jun. 12, 1964 JP Japan .................................. 39-3301S ganic amines and water. The solution is applied to the 51) Int. Cl’................................................ A61K7/09 hair and does not require an oxidizing treatment. 52 U.S. C. .................... 58) Field of Search .......................................... 424/72 6 Claims, No Drawings 4,192,863 1 2 deodorization in air for about four weeks. Accordingly, COMPLETELY ONE-STEP PERMANENT WAVE the conventional one-step permanent wave solutions are SOLUTION AND A METHOD FOR USING THE not true one-step ones but actually belong to the two SAME step solutions. As seen from the above, the conventional two-step or CROSS-RELATED APPLICATIONS one-step permanent solutions takes at least 120 minutes This application is a continuation-in-part of copend to complete the permanent waving and such a long ing Application Ser. No. 363,735 filed May 24, 1973, application period represents a troublesome drawback. now abandoned, which in turn is a continuation-in-part Furthermore, the conventional permanent wave solu of application Ser. No. 735,203 filed June 7, 1968 and 10 tions generally contain 1 to 10% by weight of thiogly now abandoned, in turn a continuation-in-part of Ser. colic acid for dissolving and softening the hair whereby No. 459,879 filed May 28, 1965 and now abandoned, in cystine and by-products of cysteine contained in the turn a continuation-in-part of Ser. No. 80,758 filed Jan. hair dissolve out and react with the second solution to 5, 1961 and now abandoned. inevitably produce hydrogen cyanide and other cyano 15 compounds as pollutants which can produce chemical FIELD OF THE INVENTION poisoning, such as pernicious anemia, cirrhosis of the The present invention relates to a one-step permanent liver or the like, and the thioglycolic acid retained in the wave solution and to a method for using the same, and hair renders the hair porous, coarse, non-sleek and dis particularly to an improvement in the one-step perma colored. nent wave solution of the present inventors's Japanese 20 Permanent wave solutions are disclosed in U.S. Pat. Pat. No. 299,121 by increasing the content of oxy Nos. 3,025,218 (Strain et al), 2,631,965 (Schnell) and organic acid from 0.01-0.03% to 0.1-0.4% by weight 3,148,126 (Martin). and adding an emulsifier of monoethanolamine, diethan In U.S. Pat. No. 3,025,218, a large amount of oxyor olamine, triethanolamine or a mixture thereof in an ganic acid of tartaric acid is used only for lowering the amount of 0.01 to 1.0% by weight of the solution. 25 pH of the permanent wave solution but still causing the BACKGROUND dissolved and softened hair to have a bad smell, and The permanent wave solutions now widely employed accordingly, a setting agent for the oxidation is required in the world are classified into the following two main whereby the applied hair is greatly damaged. In U.S. Pat. groups in respect of the application method. No. 2,631,965, 1 to 10% by weight of thioglycolic acid (1) Two-step permanent wave solution. and a large amount of oxy-organic ammonium salt are This solution is widely employed in professional contained in alkaline aqueous solution, the hair is discol beauty parlors and the application method comprises ored and a bad smell is produced, and for quick deodor tightly winding on about 60 to 100 rods having diame ization in beauty parlors, it is necessary to use a setting ters of about 2 to 10 mm, hair which is coated with a 35 agent for oxidation to remove the bad smell and accord first solution practically containing 5 to 8% by weight ingly, the solution is actually a two-step solution which of alkali thioglycolate or a modification thereof as a damages the hair. In U.S. Pat. No. 3,148,126, the perma main component. This winding operation takes about 20 nent wave solution contains 1 to 15% by weight of minutes. Then the wound hair is again coated with the thioglycolate and monoethanolamine, and still requires aforesaid solution and a vinyl cap is placed on the head 40 a setting agent for oxidation (containing hydrogen per of the user for about 10 to 30 minutes until the solution oxide and tartaric acid), heating at a high temperature of is dissolved and softens the hair surface. Then the hair is 150 to 200 F. or delivering oxygen gas under a helmet coated with a second solution containing about 2 to 6% covering the scalp for quick deodorization and wave by weight of a strong oxidizing agent such as potassium fixing. Accordingly, this permanent wave solution bromate, sodium bromate, hydrogen peroxide, or the 45 properly belongs to the two-step solution whereby the like, or with oxygen gas for about 20 to 30 minutes to fix applied hair is greatly damaged. and deodorize the dissolved and softened hair. The hair The present inventor has made a special study of hair is then unwound from the rods and subjected to a damage due to the application of the conventional per warm-rinse for about 5 to 10 minutes. The hair is then manent wave solutions and has obtained Japanese Pat. coated with a hair setting lotion and wound on 30 to 60 SO No. 299,121. He has further improved the permanent curling rollers having diameters of 1 to 3 cm to produce wave solution according to Japanese Pat. No. 299,121 large curls of 2 to 6 cm diameter according to prefer to arrive at the present invention. The permanent wave ence. This takes about 20 minutes. The hair is then dried solution of Japanese Pat. No. 299,121 is a completely with hot air at a temperature of about 45 C. for about one-step permanent wave solution comprising 3 to 3.5% 25 minutes, after which the hair is unwound from the 55 by weight of thioglycolic acid, 0.01 to 0.03% by weight rollers, and brushed and arranged with a comb and of oxy-organic acid and 1 to 2% by weight of ethyl hairpins to complete the hair-dressing. alcohol, and caustic alkali in an amount of 0.1% or less (2) One-step permanent wave solution. by weight is added to adjust the pH of the solution to This solution comprises almost the same composition 7.0 to 11.0. as that of the above-mentioned first solution which dissolves and softens the hair and the application SUMMARY OF THE INVENTON method thereof in professional beauty parlors necessar The present inventor has found that surprisingly su ily employs the above-mentioned second solution to perior effects with respect to deodorization and waving remove the bad smell of hydrogen sulfide and the like are obtained by particularly enriching the above con produced by the decomposition of the thioglycolate 65 tents of oxyorganic acid from 0.01-0.03% to 0.1-0.4% when applied. Otherwise, the bad smell cannot be re by weight and adding an emulsifier of monoethanol moved at one time and it becomes necessary to fully amine, diethanolamine, triethanolamine or a mixture water-rinse the hair and to subject the hair to natural thereof in an amount of 0.01-1.0% by weight of the 4,192,863 3 4 solution and 1.0-10.0% by weight of ethyl alcohol. The present invention is based on the following hair waving theory. -S-H H-O-S- -Hol -S-S- It has been considered that conventional permenent Cut sulfur linking Sulfur linking waving is carried out by cutting off the sulfur linking In this case, the generation of hydrogen sulfide (H2S) (-S-S-) of cystine from thioglocylic acid can be prevented by the adsorp tion of the organic amine and ethyl alcohol contained in the permanent wave solution of the present invention. Further, owing to the fact that no application of an oxidizing agent is made to the hair, the present wave ( solution never generates hydrogen cyanide and neither damages the hair nor causes the porousness of the hair, in keratin, which is a kind of protein and constitutes while also the production cost becomes very low. hair, by means of hydrogen atoms contained in the first 15 In short, the present invention can not be seen to flow solution (a reducing agent such as thioglycolic acid) to from the prior art, and the unique and characteristic produce cysteine (HS-CH2CH(NH2)COOH) which advantages of the present invention are as follows: can be easily curled, and then by fixing by means of (i) The permanent
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