AU783102B2

AU783102B2 - Composition for the permanent waving of human hair

Info

Publication number: AU783102B2
Application number: AU46023/01A
Authority: AU
Inventors: Burkhard Rose; Jorg Schneider; Jonathan Wood
Original assignee: KPSS Kao Professional Salon Services GmbH
Current assignee: Kao Germany GmbH
Priority date: 2000-05-18
Filing date: 2001-05-17
Publication date: 2005-09-22
Anticipated expiration: 2021-05-17
Also published as: AU4602301A; EP1155678A1; ATE318640T1; EP1155678B1; JP2001328924A; DE50109031D1; DE10024671A1

Abstract

Composition for durably reshaping hair comprises a thiol reducing agent and a mixture of: (a) 0.25-7.5 wt.% ethyl alcohol, n-propyl alcohol and isopropyl alcohol; (b) 0.25-7.5 wt.% pentanediol, hexanediol and methylpentanediol; and (c) 0.25-7.5 wt.% 1-(m)ethoxypropanol and diethylene glycol monomethyl (ether).

Description

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AUSTRALIA

Patents Act 1990 Goldwell GmbH x- V.ao SU6c-\

ORIGINAL

COMPLETE SPECIFICATION STANDARD PATE NT

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Invention Title: Composition for the permanent waving of human hair The following statement is a full description of this invention including the best method of performing it known to us:- 000 The present invention concerns a composition for the permanent waving of human hair which has an excellent waving effect while not exerting any damaging effect on the hair, even upon repeated application.

It is generally known that permanent waving is carried out in two steps: The reductive splitting of the cysteine disulfide bonds in the hair by a reducing agent, and the subsequent neutralization by application of an oxidizing agent, whereby the cysteine disulfide bonds are restored.

The reducing agent still most frequently used today is thioglycolic acid, in particular its ammonium salt, although. numerous other thio compounds have been proposed 0 for this purpose, which, however, mostly did not succeed.

The compositions containing thioglycollates are customarily applied at a pH-value between 8 and 10, in particular 8.5 and 9.5. However, upon repeated application at S close intervals this can lead to hair damage.

Efforts have already been made to overcome this disadvantage by creating so-called S"acid permanent waving compositions" with an application pH-value between about 6.8 to 7.8, i.e. ranging around the neutral point. The reducing agent most frequently used in these compositions is thioglycolic acid monoglycerol ester. This substance, however, has proven to exert a skin-irritating, in particular sensitizing effect on many users, so that this solution is also not ideal.

The present invention is directed to permanent waving compositions which are not damaging to hair and yet have a good waving performance.

In one aspect. the present invention is directed to a composition for the permanent waving of human hair. comprising at least one thio compound with a reducing effect, preferably thioglycolic acid and/or thiolactic acid or the salts thereof. as well as a combination of a) about 0.25 to about 7.5 by weight of ethyl alcohol, n-propyl alcohol and/or isopropyl alcohol; b) about 0.25 to about 7.5 by weight of at least one component selected from the group pentanediols, hexanediols and/or methyl pentanediols; and c) about 0.25 to about 7.5 by weight of at least one component from the group 1-methoxypropanol(-2), 1-ethoxypropanol(-2) and/or diethyleneglycol monomethyl or monomethyl ether, each calculated to the total ready-to-use composition.

o 1 EP 666 073 A2 already discloses permanent waving compositions containing similar solvent mixtures, whereby the component however, consists of at least component selected from the group 1.2-propanediol, 1.2-butanediol, 1.3-butanediol, glycerin and/or dipropyleneglycol monomethyl ether.

15 Surprisingly, it was found, however, that their use according to the invention achieves an improved waving performance through pentane, methyl pentane and/or hexanediols, also enhancing the dermatological compatibility of the total composition.

According to a preferred embodiment of the invention, the ready-to-use permanent waving composition destined to be applied to the hair shows a pH-value between o about 6.5 and 10.5, in particular 7.0 to about As explained above, as preferred thio compound with a reducing effect, the 5 permanent waving composition according to the invention contains thioglycolic acid and/or 2- or 3-thiolactic acid, or the salts thereof, for example, diammonium or alkali salts.

However, the use of other thio compounds with a waving capability is also possible, ;o for example, the thioglyceryl-C 1

-C

20 -alkyl ether or 1-phenyl-2-mercapto ethanol known from EP-A 235 783, as well as the C 1

-C

20 -alkyloxy ethoxy thioglyceryl ethers disclosed in EP-A 461 526.

Further useful thio compounds are in particular cysteine or the hydrochloride thereof, homocysteine, cysteamine, N-acetyl cysteine, thioglycerol, ethanediol monothioglycollate, 1.2-propyleneglycol monothioglycollate (see also WO-A 93/1791), 1-3-propanediol monothioglycollate or the isomer mixture resulting therefrom, 1.3-butanediol and 1.4-butanediol monothioglycollate and the isomer mixtures therefrom, ethanediol monothiolactate, 1.2-propanediol and 1.3 propanediol monothiolactate and the isomer mixtures thereof, 1.3-butanediol and 1.4-butanediol monothiolactate and the isomer mixtures thereof, polyethylene glycol, such as di-, tri- and tetraethyleneglycol monothioglycollates and monothiolactates, 1o polypropylene glycol, such as di-, tri- and tetrapropylene glycol monothiolactates and monothioglycollates, glycerol monothiolactate and further thio acids and the esters thereof, as well as their mixtures.

The total reducing agent content in the compositions according to the invention customarily amounts from 2.5 to about 15 by weight, calculated to the free thioglycolic acid as reference substance.

The use of inorganic sulfites, in particular alkali sulfites and alkali hydrogen sulfites, for example, sodium sulfite is basically also possible.

The waving compositions containing reducing agents can, if necessary, comprise alkalizing agents. Their quantity is dependent on the reducing agent and the desired pH-value of the composition. Reducing agent compositions preferably contain from about 0.1% to about in particular about 0.5% to about 2.5% by weight thereof, 25 calculated to the total composition.

Alkalizing agents preferred within the scope of the invention are ammonium carbamate, ammonia and/or ammonium(bi)carbonate. As stated above, it is desirable to adjust the pH-value between about 6.5 and 10, preferably about 7 to o0 The alkalizing agent can be present in a single phase together with the thio compound constituting the waving effect; however, for reasons of compatibility and stability it may also be meaningful to keep both substances in a form separate from each other until application, for example in two-component containers, which are not mixed until immediately prior to application upon the hair.

The permanent waving compositions used according to the invention preferably also contain surfactants. Their proportion ranges from about 0.1 to about 10%, in particular from about 1 to about 5 by weight of the composition containing the reducing agent.

The surfactants used both in the reduction agent compositions and in the neutralizer io compositions are preferably the known anionic products, which are used optionally also in combination with nonionic surfactants.

Suitable anionic surfactants are especially the known alkyl ether sulfates and carboxylic acids, in particular in form of their alkali salts, as well as protein fatty acid condensates.

Suitable nonionic surfactants are in particular C 8

-C

18 -fatty alcohol polyglycol ethers, fatty acid polyglycol esters, fatty acid alkanolamides, amineoxides, and especially

C

8 -Cis-alkyl polyglucosides.

Also possible is the incorporation of amphoteric surfactants, such as the known betaines and amido betaines, as well as cationic surfactants, such as quaternary ammonium compounds.

5 The second substance essential according to the invention, at least one compound from the group ethyl alcohol, n-propyl alcohol and/or isopropyl alcohol, is present in an amount of 0.25 to about 7.5 by weight, preferably from about 0.5 to 5 by weight, in particular about 0.75 to 2.5 each calculated to the total composition. The substance of choice is isopropyl alcohol.

The third essential component, at least one component from the group pentanediols, hexanediols and/or methyl pentanediols is also present in an amount from 0.25 to about 7.5 preferably from about 0.5 to about 5 by weight, calculated to the total ready-to-use composition. Preferred are 1.2- and 1.5-pentanediol, 1.6hexanediol, 3-methyl-1.5-pentanediol and 2-methyl-2.4-pentanediol, preferably in an amount ranging from about 0.5 to about 3 by weight.

The last component essential according to the invention, 1-methoxypropanol(-2), 1-ethoxypropanol(-2),and/or diethyleneglycol monomethyl or monoethyl ether, is also present in an amount ranging between about 0.25 and about 7.5 by weight, calculated to the total ready-to-use composition. Preferred are diethylene-glycol monoethyl ether, also known as ethoxydiglycol or ethyl carbitol, and 1-methoxypropanol(-2) in an amount between about 1 and about 5 by weight.

Io The permanent waving compositions according to the invention can comprise all additives proposed and used for this purpose.

To avoid repetition, reference is here made to the known state of the art and the 15 summaries thereof, for example in "Ullmann's Encyclopaedia of Industrial Chemistry", Vol. A12 (1986), pages 588 to 591, as well as to the monography of K.

Schrader, "Grundlagen und Rezepturen der Kosmetika", 2 nd Ed. (1989, Huthig Buchverlag) pages 823 to 840.

.o0 In the event that the composition is present in two phases kept separate from each other until application, it is advantageous to adjust the pH-value of one phase in the acidic range, for example, between about 4.5 and This is carried out, for example, by adding an amino acid hydrochloride, in particular 15 cysteine hydrochloride, which also serves to further enhance the waving effect, and glycine hydrochloride.

However, it is also possible to add further amino acid hydrochlorides, for example, those of alanine, valine, leucine, isoleucine, proline, tryptophane, phenyl alanine, oo methionine, serine, tyrosine, threonine, asparagine, glutamine or histidine.

The proportion of the amino acid hydrochloride is determined by the adjustment of the required pH-value; the minimum proportion is about 0.5 by weight, the maximum proportion being about 5 by weight, calculated to the pure amino acid and the total composition, the sum of the compositions stored separately until application).

In such two-component preparations, the composition comprising the alkalizing ammonium salt then has an alkaline pH-value, preferably in the range of about 8 and The hair permanently waved by application of the permanent waving composition according to the invention is then neutralized by known and customary neutralizing agents, namely hydrogen peroxide or alkali bromates.

In the event that the compositions according to the invention are present in separate .0i /o phases until application, separate storage of the compositions until their use is preferably carried out in the known two-chamber containers, the separating wall of which is destroyed by appropriate means upon application.

Such two-chamber containers, which are particularly suited for the compositions according to the invention, are described, for example, in the German Disclosures 2 8 5 2 5 3 6 06 003, 38 12 343 and 38 37 595.

o* *e *•oe Thus, the present invention is also directed to a composition as hereinbefore described, characterised in that it consists of two compositions kept separately until their application, whereby one composition contains at least one amino acid salt in aqueous medium and has a pH-value adjusted in the range 4.5 and 6.5, and a second composition kept separately therefrom, contains ammonium hydrogen carbonate, ammonium carbonate and/or ammonium carbamate and shows a pH-value in the range 8 and and both compositions are admixed immediately prior to application onto human hair to form a ready-to-use composition (AB) which has a pH-value in the range 7 and 8.

Preferably, the reducing thio compound is at least partially contained in composition Any discussion of documents, acts, materials, devices, articles or the like which has been included in the present specification is solely for the S: 15 purpose of providing a context for the present invention. It is not to be taken :ooo *as an admission that any or all of these matters form part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed in Australia before the priority date of each claim of this application.

20 Throughout this specification the word "comprise", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated element, integer or step, or group of elements, integers or steps, but not the exclusion of any other element, integer or step, or group of elements, integers or steps.

The following Examples illustrate the invention.

o* *.i .7 8 Example 1 Permanent Waving Composition for Normal Hair Composition A: Ammonium hydrogen carbonate 4.5 (g) Cationic polymer Nonionic solubilizer 0.8 (ethyleneoxide condensate) Isopropyl alcohol to Diethyleneglycol monoethyl ether Cocoamidopropyl betaine Turbidifying agent, perfume q.s.

Ammonia, 25% pH 8.4 Water 72.0 Composition B: So• Ammonium thioglycollate, 70% 18.0 (g) 2-Thiolactic acid 2 -Methyl-2.4-pentanediol 0 Ammonia, 25% pH Water 28,0 The Compositions A and B were packed separately into a customary two-chamber can.

When the two Compositions were mixed, a product with a pH-value of 7.4 was obtained, which achieved an excellently formed permanent wave without any damage to the hair upon application in a customary permanent waving treatment with subsequent peroxide neutralization.

9 Example 2 Neutral Permanent Waving Composition for Dyed Hair Composition A: Ammonium hydrogen carbonate Cationic polymer Nonionic solubilizer (ethoxylate) 'o Perfume Ethanol 1-Methoxypropanol(-2) Ammonia, 25% Water Composition B: Ammonium thioglycollate, 70% 2-Thiolactic acid 1.6-Hexanediol Ammonia, 25% Water 0.3 pH 8.3 72.0 3.5 (g) 0.8 13.0 (g) pH 28.0 Packaging and application of the Compositions A and B were carried out as described in Example 1.

The ready-to-use total composition showed a pH-value of 7.4._ .1 Example 3 Permanent Waving Composition for Normal Hair Ammonium hydrogen carbonate Ammonium thioglycollate, 60% 2-Methyl-2.4-pentanediol n-Propanol Nonionic solubilizer 1o Cationic polymer Perfume Ethoxydiglycol Ammonia, 25% Water 5.0 (g) 21.3 0.7 0.3 pH 8.3 100.0 After neutralization with peroxide, this Composition also resulted in an expressive permanent wave; no hair damage could be found, even upon several repeated applications.

Example 4 Permanent Waving Composition for Damaged Hair 57 Ammonium hydrogen carbonate Ammonium thioglycollate, 60% 1 .5-Pentanediol Nonionic solubilizer Perfume 1. Ethanol 1 -Methoxypropanol(-2) Ammonia, 25% Water 15 The achieved permanent waving result was for the Composition used in Example 3.

2.5 (g) 15.0 0.7 0.3 PH 100.0 of good quality, similar to that described a a.

a a a

Claims

1. Composition for the permanent waving of human hair, comprising at least one thio compound with a reducing effect and a combination of a) 0.25% to 7.5% by weight of ethyl alcohol, n-propyl alcohol and/or isopropyl alcohol; b) 0.25% to 7.5% by weight of at least one component from the group pentanediols, hexanediols and/or methyl pentanediols; and c) 0.25% to 7.5% by weight of l-methoxypropanol(-2), 1-ethoxy- propanol(-2) and/or diethyleneglycol monomethyl or monomethyl ether, each calculated to the total composition.

2. Composition according to claim 1, wherein the composition destined for application onto the hair has a pH-value in the range 7 and

3. Composition according to claim 1 or 2, characterized in that it contains thioglycolic acid and/or 2-thiolactic acid or the salts thereof as the thio 15 compound having a reducing effect.

4. Composition according to any one of claims 1 to 3, characterized in that as component b) it contains 1.2-pentanediol, 1.5-pentanediol, 1.6- hexanediol and/or 2-methyl-2.4-pentanediol in an amount of 0.5 to 5% by weight, calculated to the total composition. 20

5. Composition according to any one of claims 1 to 4, characterized in that as component c) it contains 1% to 5% by weight, calculated to the total composition, of diethyleneglycol monoethyl ether.

6. Composition according to any one of claims 1 to 5, characterized in that it contains 0.5% to 5% by weight, calculated to the total composition, of ammonium hydrogen carbonate, ammonium carbonate and/or ammonium carbamate.

7. Composition according to any one of claims 1 to 6, characterized in that it consists of two compositions kept separately until their application, whereby one composition contains at least one amino acid salt in aqueous medium and has a pH-value adjusted in the range 4.5 and 6.5, and a second composition kept separately therefrom, contains ammonium hydrogen carbonate, ammonium carbonate and/or ammonium carbamate and shows a pH-value in the range 8 and 9.5, and both compositions are admixed immediately prior to application onto human hair to form a ready-to-use composition (AB) which has a pH-value in the range 7 and 8. 13

8. The composition according to claim 7, wherein the reducing thio compound is at least partially contained in the composition

9. A composition according to claim 1 substantially as hereinbefore described with reference to the examples and/or the preferred embodiments and excluding, if any, comparative examples. Dated this twenty-fourth day of May 2005 KPSS-Kao Professional Salon Services GmbH Patent Attorneys for the Applicant: F B RICE CO 0 0 0 m:\specifications\1 00000\1 05513clmmjc.doc