EP0576507A1

EP0576507A1 - Process for the permanent waving of hair

Info

Publication number: EP0576507A1
Application number: EP19920906778
Authority: EP
Inventors: Jörg KAHRE; Reinhard Müller; Adolf Klenk
Original assignee: Henkel AG and Co KGaA
Current assignee: Henkel AG and Co KGaA
Priority date: 1991-03-27
Filing date: 1992-03-18
Publication date: 1994-01-05
Also published as: DE4109976A1; WO1992017155A1

Abstract

On peut fortement améliorer les propriétés de cheveux ondulés par une permanente en utilisant une composition de substances actives dont (a) un acide carboxylique de pyrrolidone ou ses sels ayant la formule générale (I), dans laquelle au moins un des substituants R1 à R3 désigne un groupe- COOR4, où R4 désigne hydrogène, un ion métal alcalin, un ion métal alcalino-terreux ou un ion ammonium +NHR5R6R7, où R5 à R7 désignent indépendamment les uns des autres hydrogène, des groupes alkyle ayant 1 à 22 atomes de C, des groupes hydroxyalkyles ayant 1 à 4 atomes de C, des groupes alcényle ayant 2 à 22 atomes de C, des groupes acyle ayant 2 à 22 atomes de C ou des groupes aromatiques éventuellement substitués ayant 6 à 10 atomes de C, alors que les substituants restants (R1 à R3) désignent hydrogène ou des groupes alkyle ayant 1 à 4 atomes de C.; ainsi que (B) un autre composé (B), sélectionné dans le groupe comprenant panthénol, des dérivés de panthénol, allantoïne, huiles de silicone et des hydrolysats de protéines. Les substances actives peuvent être associées ou réparties indifféremment dans la solution d'ondulation, dans la solution de fixation ou dans une solution de rinçage.The properties of wavy hair can be greatly improved by a perm using a composition of active substances including (a) a pyrrolidone carboxylic acid or its salts having the general formula (I), in which at least one of the substituents R1 to R3 denotes a group - COOR4, where R4 denotes hydrogen, an alkali metal ion, an alkaline earth metal ion or an ammonium ion + NHR5R6R7, where R5 to R7 denote, independently of each other hydrogen, alkyl groups having 1 to 22 C atoms , hydroxyalkyl groups having 1 to 4 C atoms, alkenyl groups having 2 to 22 C atoms, acyl groups having 2 to 22 C atoms or optionally substituted aromatic groups having 6 to 10 C atoms, while the remaining substituents (R1 to R3) denote hydrogen or alkyl groups having 1 to 4 C atoms; as well as (B) another compound (B), selected from the group comprising panthenol, panthenol derivatives, allantoin, silicone oils and protein hydrolysates. The active substances can be combined or distributed in the ripple solution, in the fixing solution or in a rinsing solution.

Description

"Process for permanent shaping of hair"

The invention relates to a method for permanent hair shaping by reductive splitting and renewed oxidative knotting of disulfide bonds in hair keratin.

The permanent hair shaping is carried out according to the known permanent wave method in such a way that the hair is mechanically deformed and the deformation z. B. by winding on hair rollers or papillots. Before and / or after this shaping, the hair is treated with the aqueous preparation of a keratin-reducing substance and rinsed with water or an aqueous solution after an exposure time. In a second step, the hair is then treated with the aqueous preparation of an oxidizing agent. After an exposure time, this is also rinsed out of the hair and the hair is freed from the mechanical shaping aids (curlers, papillots).

The aqueous preparation of the keratin-reducing agent is usually made alkaline, so that the hair swells and in this way a deep penetration of the keratin-reducing substance into the hair is made possible. The keratin-reducing substance cleaves part of the disulfide bonds of keratin to -SH groups, so that the peptide crosslinking is loosened and, as a result of the tension in the hair due to the mechanical deformation, the keratin structure is reoriented. Under the influence of the oxidizing agent, disulfide bonds are again formed, and in this way the keratin structure is re-fixed in the predetermined deformation.

Neither the swelling effect of the alkali nor the keratin-splitting effect of the reducing agent can be completely reversed; The freshly permed hair is therefore very sensitive to mechanical stress. Too strong a reduction level - e.g. B. due to too high concentration of keratin-reducing substance or too long exposure time - can also lead to severe hair damage, which manifests itself, for example, in embrittlement or dulling of the hair. Furthermore, in In many cases, other properties such as wet and dry combability, grip, smoothness, softness, gloss and tear resistance are only unsatisfactory.

In DE-OS 38 26 369 it was therefore proposed to add a cationic surfactant and / or a cationic polymer and a salt of 2-pyrrolidone-5-carboxylic acid to the fixing solution in addition to the oxidizing agent. Although this results in improved conditioning of the deformed hair, the general problem also addressed in the publication remains that cationic compounds in many cases adversely affect the result of the shaping and the rinsing out of the fixing agent.

There was therefore still the task of finding a method of permanent hair shaping in which the risk of undesirable side effects is avoided with greater certainty.

It has now surprisingly been found that a significant improvement in the properties of permed hair is achieved by using special combinations of active ingredients in the agents used during the waving process.

The invention therefore relates to a process for permanent shaping of hair, in which the hair is prepared before and / or after mechanical shaping with the aqueous preparation of a keratin-reducing agent

Treated substance, rinsed after an exposure time, then fixed with an aqueous preparation of an oxidizing agent and also rinsed after an exposure time, characterized in that in at least one of the aqueous solutions and / or at least one of the rinses a compound (A) of the general formula (I),

in which at least one of the substituents R ¹ to R ³ represents a group -COOR ⁴ , in which R ^{4 is} hydrogen, an alkali metal ion, an alkaline earth metal ion or an ammonium ion ⁺ NHR ⁵ R ⁶ R ⁷ , in which R ⁵ to R ^{7 are} independent of one another Are hydrogen, alkyl groups with 1 to 22 carbon atoms, hydroxyalkyl groups with 1 to 4 carbon atoms, alkenyl groups with 2 to 22 carbon atoms, acyl groups with 2 to 22 carbon atoms or optionally substituted aromatic groups with 6 to 10 carbon atoms , and the remaining substituents R ¹ to R ^{3 represent} hydrogen or alkyl groups having 1 to 4 carbon atoms, and at least one further compound (B) selected from the group consisting of panthenol, derivatives of panthenol, allantoin, silicone oils and protein hydrolyzates includes, is included.

The aqueous preparation of the keratin-reducing substance is referred to below as the waving agent and the aqueous preparation of the oxidizing agent is referred to as the fixing solution.

It has been found that a positive effect for the hair is achieved regardless of whether the compounds (A) and (B) are used in the waving agent, in the fixing solution or in one of the two rinses. The occurrence of the effect is also independent of whether both components are present in the same preparation or in different means.

Particularly large effects have been found when compounds (A) and (B) are contained in the waving agent and / or the fixing solution. Especially in the cases where the compound (A) was contained in the fixing solution, the impairment of the hair caused by the waving process was very slight.

The compounds (A) are derivatives of 2-pyrrolidone. Preferred derivatives are the 2-pyrrolidone-3-, -4- and -5-carboxylic acid and its salts. Preferred salts of these compounds are the sodium, potassium, calcium, magnesium and those ammonium salts in which the ammonium ion carries, in addition to hydrogen, one to three C ₁ -C ₄ -alkyl groups. Particularly preferred compounds (A) are 2-pyrrolidone-5-carboxylic acid and its salts. The sodium salt is very particularly preferred.

A further component for achieving the desired effect is a compound (B) selected from the group panthenol, derivatives of panthenol, allantoin, silicone oils and protein hydrolyzates.

Preferred derivatives of panthenol are pantethine, as well as pantothenic acid and its alkali metal and ammonium salts.

The following compounds can be used as silicone oils:

Oligomeric polydimethylcyclosiloxanes (CTFA name: Cyclomethicone), in particular the tetrameric and pentameric compound,

Hexamethyl disiloxane,

Polyphenylmethylsiloxane (CTFA name: Phenyl Trimethicone),

Dimethylsiloxane-dimethylpolysiloxanol mixtures (CTFA name: Cyclomethicone (and) Dimethiconol),

Silicon-glycol copolymers (CTFA name: Dimethicoπe Copolyol), amino-functional polydimethylsiloxanes and

hydroxylamino modified silicones.

Such connections are available on the market. Known commercial products are, for example, DC ^R 344 Fluid, DC ^R 345 Fluid, DC ^R 200 Fluid, DC ^R 556, DC ^R 1? 0, DC ^R 193 SU, DC ^R Q2-1401 and DC ^R 929 from the manufacturer Dow Corning and the products Abil ^R K4, Abil ^R K520 and Abil ^R B8839 from the manufacturer Th. Goldschmidt AG.

Protein hydrolyzates are product mixtures that are obtained by acidic, basic or enzymatically catalyzed breakdown of proteins (proteins).

The following hydrolysates can be used according to the invention:

Collagen hydrolyzates (CTFA names: Hydrolyzed Animal Protein, Hydrolyzed Animal Collagen and Soluble Animal Collagen). Hydrolyzates Base bovine collagen may be preferred. The hydrolysates can also be in the form of salts, for example as the sodium or ammonium salt.

Known commercial products are, for example, Dehylan ^R ET 40 (Henkel), Promois ^R Silk 1000 Q (Interorgana), Collapuron ^R N (Henkel), Nutrilan ^R V 37908 and Nutrilan ^R I (Grünau), Gelita-Sol ^R C and CS (Deutsche Gelatine Factories Stoess & Co) as well as Lexein LP 170 and Lexein ^R X-350 (Inolex).

Collagen hydrolyzate condensates. According to the invention, collagen hydrolyzates can also be used in the form of their condensates with organic acids, in particular fatty acids or fatty acid mixtures. Preferred acids are oleic acid, myristic acid, undecylenic acid, coconut fatty acid and abietic acid. The condensation products can also be in the form of salts, in particular sodium, potassium and triethanolamine salts. Such condensation products also carry the CTFA names Oleoyl Hydrolyzed Animal Protein, Myristoyl Hydrolyzed Animal Protein, Oleoyl Hydrolyzed Animal Collagen, Potassium Coco Hydrolyzed Animal Protein, TEA Abietoyl Hydrolyzed Animal Collagen, Potassium Undecylenoyl Hydrolyzed Animal Collagen and TEA Coco Hydrolyzed Animal Collagen.

Commercial products include Lamepon ^R LP0, Lamepon ^R 4 SK, Lamepon ^R UD, Lamepon ^R 460, Lamepon ^R PA TR, Lamepon ^R ST 40 and Lamepon ^R S (Grünau) as well as Lexein ^R A 240, Lexein ^R S 620 and Lexein ^R A 520 (Inolex).

Cationized collagen hydrolyzates such as, for example, the product on the market under the name Lamequat ^R L (CTFA name: Lauryldimonium hydroxypropylamino hydrolyzed animal protein; Grünau) can also be used according to the invention.

Elastin hydrolyzates (CTFA name: Hydrolyzed Animal Elastin).

Examples of elastin hydrolyzates which can be used according to the invention are the products sold under the names Nutrilan ^R Elastin E 20 (Henkel) and Gelita ^R Gelastin (Deutsche Gelatine Fabriken Stoess & Co). Bovine elastin hydrolyzates may be preferred. In the aqueous preparation for carrying out the second stage, the oxidative fixation, z. B. hydrogen peroxide and the usual stabilizers for stabilizing aqueous hydrogen peroxide preparations may be included. The pH of such aqueous H ₂ O ₂ preparations which contain about 0.5 to 3.0% by weight of H ₂ O ₂ is preferably 2 to 4; it is adjusted by inorganic acids, preferably phosphoric acid. Other preferred oxidizing agents are sodium and potassium bromate. Such bromates are used in concentrations of 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.

In addition to the oxidizing agent, further auxiliaries and additives known for this purpose can be contained in the aqueous preparation for carrying out the second stage of the hair shaping process according to the invention. B. surfactants, quaternary ammonium salts, cationic polymers, fragrances and opacifiers.

Both Wellotion and fixative can be formulated as a cream, gel or liquid. It may be preferred to package the preparations in the form of foam aerosols, which are mixed with a liquefied gas such as, for. B. propane-butane mixtures, N ₂ O, dimethyl ether, fluorocarbon blowing agents or mixtures thereof are filled in aerosol containers with a foam valve.

The following examples are intended to explain the subject matter of the invention in more detail:

Condensation products of elastin hydrolyzates with fatty acids such as lauric acid (CTFA name: Lauroyl Hydrolyzed Animal Elastin) can also be used. Crolastin ^R AS (Croda) is a corresponding market product.

Keratin hydrolysates (CTFA name: Hydrolyzed Animal Keratin) represent a further group of protein hydrolysates to be used according to the invention. Examples of branded products are Nutrilan ^R Keratin W (Henkel), Kerapro ^R S (Diedrichs), Promois ^R WK H (Seiwa Oil & Chemetics) and Kerasol ^R (Croda).

Other proteins, the hydrolysates of which are compounds (B) to be used according to the invention, are wheat proteins, milk proteins, protein proteins, silk proteins, almond proteins, soy protein and proteins from animal skins. Corresponding sales products are, for example, Gluadin ^R AGP (Henkel), products of the DiaMin ^R series (Diamalt), Lexein ^R X-250 and Lexein ^R MP (Inolex), Crotein ^R A, Crotein ^R C, Crotein ^R ASC and Crotein ^R 0 ( Croda), Gelita ^R Flex S 50 (Deutsche Gelatine Fabrik Stoess & Co) and Hydrosilk ^R 10000 (Croda).

These protein hydrolyzates can also be reacted with organic acids or acid mixtures such as myristic acid, oleic acid, coconut fatty acid or abietic acid to form condensates which can be used according to the invention. Examples of corresponding commercial products are Lexein ^R A 200 (Inolex), Lamepon ^R PO-TR, Lamepon ^R PA-K, Lamepon ^R S-MV and Lamepon ^R S-TR (Grünau) and Croteiπ ^R CCT (Croda).

Quaternized products of such protein hydrolysates are available, for example, as Lexein ^R QX 3000 (Inolex), Crotein ^R Q (Croda) and Croquat ^R WKP (Croda).

Panthenol is a particularly preferred compound (B). It has proven advantageous in cases where panthenol is part of the waving agent to add the panthenol to the other components of the waving agent only immediately before use. The compounds (A) are used in the process according to the invention in amounts of 0.1 to 20% by weight, based on the total amount of the preparation or rinse containing these compounds. Amounts of 0.1 to 5% by weight are preferred.

The compounds (B) are used in the process according to the invention in amounts of 0.1 to 10% by weight, based on the total amount of the preparation or rinse containing these compounds. Amounts of 0.1 to 5% by weight are preferred.

The keratin-reducing substances which can be used in the process according to the invention are the customary mercaptans and the alkali metal salts of sulfurous acid. The alkali metal or ammonium salts of thioglycolic acid and / or thiolic acid and the free acids are preferably suitable for the process according to the invention. These can be used in the keratin-reducing preparations of the first stage of the hair shaping process according to the invention in a concentration of 0.5 to 1.0 mol / kg at a pH of 6.5 to 10. The exposure time for the keratin-reducing preparation is generally 20 to 40 minutes, with the thickness of the hair to be treated, the desired degree of deformation, the size of the mechanical shaping aid used (hair roller) and the type of keratin reducing agent being further influencing factors.

In addition to the keratin-reducing substance, all of the auxiliaries and additives known for this purpose can be contained in the aqueous preparation for carrying out the first stage of the hair shaping process according to the invention. These are primarily surface-active substances, consistency enhancers, complex containers; Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, guanidines and urea, ammonia and buffer salts for adjusting a pH of 6.5 to 10, e.g. B. ammonium carbonate, water-soluble polymers to increase viscosity, fragrance-influencing substances such as perfume oils, dimethyl isosorbitol and cyclodextrins, dyes and opacifiers. Examples

1.1 Tensile strain measurements on treated hair

Hair tresses (tress length: 15 cm / tress weight: 2 g) of the 6921 type (Fischenbach and Miller) were treated for 30 minutes with 50 ml of thioglycolic acid (8% strength by weight solution, adjusted to pH 9 with ammonia). It was then rinsed with water (35 ° C.) for 2 minutes. This procedure was repeated 5 times.

The hair was then treated with the fixing solution for 10 minutes. It was then rinsed, dried as described above and the maximum tensile strength and the 15% elongation value were determined. Details of the measurement method can be found in the literature (Physician Cosmetology 15, 347-355 (1985) and Perfumery & Cosmetics 72, 74-81 (1991).

Fixing solutions:

Component solution 1 solution 2

(according to the invention) (comparison)

[Parts by weight] [parts by weight]

Potassium bromate 3.5 3.5

Dehyton ^R K ¹ 2.0 2.0

Eumulgin ^R 286 ² 2.5 2.5

Cremophor ^R RH 60 ³ 3.0 3.0

Texapon ^R N 25 ⁴ 4.0 4.0

Ajidew ^R N 50 ⁵ 5.0 -

D-panthenol 4.0 -

Water 76.0 85.0 ¹ fatty acid amide derivative with betaine structure of the formula

R-CONH- (CH ₂ ) ₃ -N ⁺ (CH ₃ ) ₂ -CH ₂ -COO-; CTFA name: Cocamidopropyl Betaine (approx. 30% active substance in water) (HENKEL) ² polyglycol ethers; CTFA name: Nonoxynol-10 (HENKEL)

³ hydrogenated castor oil, reacted with 60 moles of ethylene oxide per mole of castor oil (BASF)

⁴ sodium lauryl ether sulfate; CTFA name: Sodium Laureth Sulfate (approx. 28% active substance in water) (HENKEL)

⁵ dl-2-pyrrolidone-5-carboxylic acid sodium salt (AJINOMOTO).

Solution 1 Solution 2

Ultimate tensile strength [mN]

after fixation with 712 572

15% elongation value [mN]

after fixation with 383 303

1.2 Determination of dry and wet combability

The dry and wet combability was determined on brown hair (Alkinco 6634, strand length: 12 cm; strand weight: 1 g) in the form of a mean pair comparison. To determine the zero value, the strands were rinsed for 1.5 minutes with water (1 l / min, 38 ° C.) and combed out. The tresses were then dried over a fan at 45 ° C. for 40 minutes. The combability was determined after conditioning for 12 hours at 30 ° C. and a relative air humidity of 40%. The tresses of hair were then treated with 100 g of the formulation for 5 minutes and then rinsed, dried and conditioned in the manner shown above. Then the combability was determined. The same procedure was followed to determine the wet combability. In contrast to the combability, the hair was rinsed for 1 minute under running water (1 l / min; 38 ° C) and then measured immediately.

The following fixing solutions were tested:

Component Solution A Solution B Solution C Solution D

(according to the invention) (comparison)

[Parts by weight] [parts by weight]

Potassium bromate 3.5 3.5 3.5 3.5

Dehyton ^R K 2.0 2.0 2.0 2.0

Eumulgin ^R 286 2.5 2.5 2.5 2.5

Cremophor ^R RH 60 3.0 3.0 3.0 3.0

Texapon ^R N 25 4.0 4.0 4.0 4.0

Ajidew ^R N 50 ⁴ 5.0 - - 5.0

D-panthenol (75%) 5.3 - 5.3 -

Water 74.7 85.0 79.7 80.0

The following combability was measured before and after treatment with solutions A - D:

Solution: dry combing wet combing

before after before after

[mJ] [mJ] A 7.2 5.8 34.3 27.6

B 6.3 6.0 32.7 37.4

C 5.6 5.5 32.7 37.4

D 6.1 5.6 33.2 38.0 2. Examples of use

2.1.a. Corrugated gel

% By weight

Thioglycolic acid 8.0

Thiolactic acid 3.0

Ammonia (25%) 9.3

Ammonium carbonate 3.0

Cremophor ^R RH 60 2.0

Natrosol ^R 250HHBR ⁶ 0.7

Turpinal ^R SL ⁷ 0.3

Kerasol ⁸ 0.5

Allantoin 0.5

Ajidew ^R N50 2.0

D-panthenol 0.2

Perfume oil q.s.

Water ad 100

⁶ hydroxyethyl cellulose (AQUALON)

⁷ l-hydroxyethane-1,1-diphosphonic acid; CTFA name: Etidronic Acid

(HANDLE)

⁸ keratin hydrolyzate with an average molecular weight of 100,000 daltons (CRODA)

2.1.b. Fixation

% By weight

Hydrogen peroxide (50%) 6.0

Sodium hydroxide solution (45%) 0.8

Cremophor ^R RH 60 4.0

Turpinal ^R SL 0.4

Keltrol ^R 9 0.1

Kerasol ^R 0.5 D-panthenol 1.0

Ajidew ^R N 100 ¹⁰ 4.0

Perfume oil q.s.

Water ad 100

9 xanthan gum (KELCO)

10 DL-2-pyrrolidone-5-carboxylic acid (AJINOMOTO)

2.2.a. Corrugated cream

% By weight

Thioglycolic acid 8.0

Ammonia (25%) 7.3

Ammonium carbonate 3.0

Lanette ^R O ¹¹ 5.0

Eutanol ^R G ¹² 4.0

Turpinal ^R SL 0.3

Texapon N 25 2.0

Nutrilan ^R I 50 ¹³ 2.0

Allantoin 2.0

Ajidew N 50 2.0

Perfume oil q.s.

Wasser ad 100 ¹¹ Mixture of higher, saturated fetal alcohols, mainly cetyl and

Stearylafkoholf CTFA name: Cetearyl Alcohol) (HENKEL)

¹² 2-octyl-dodecanol, condensation product from saturated liquid

Fatty alcohols, mainly decyl alcohol, manufactured according to the

Guerbet reaction; CTFA name: Octyldodecanol (HENKEL)

¹³ partial protein hydrolyzate from degraded bovine collagen (50%) (CHEMISCHE FABRIK GRÜNAU) 2.2.b. Fixation

% By weight

Potassium bromate 3.5

Citric acid 0.2

Cremophor ^R RH 60 4.0

Trilon ^R ASl ⁴ 0.3

Lamequat ^R L ¹⁵ 1.0

D-panthenol 3.0

Ajidew ^R N 50 3.0

Perfume oil q.s.

Water ad 100

¹⁴ nitrilotriacetic acid (BASF)

¹⁵ cationized collagen hydrolyzate; CTFA name: Lauryldimonium hydroxypropylamino hydrolyzed animal protein (CHEMISCHE FABRIK GRÜNAU)

2.3.a. liquid wellotion

% By weight

Thioglycolic acid 7.0

Ammonia (25%) 6.4

Ammonium carbonate 3.0

Dehyton ^R AB 30 ¹⁶ 3.0

Trilon ^R AS 0.3

Nutrilan ^R Keratin W ¹⁷ 1.0

Perfume oil, dye q.s.

Water ad 100 ¹⁶ fatty amine derivative with betaine structure; CTFA name: Coco-betaine

(HANDLE)

1 ⁷ Merino virgin wool hydrolyzate; CTFA name: Hydrolyzed Animal

Keratin (HENKEL) 2.3.b. Fixation

% By weight

Potassium bromate 3.5

Citric acid 0.1

Texapon ^R N 25 4.5

Keltrol ^R 0.3

Dehyquart ^R E ¹⁸ 1.0

Gelita-Sol ^R CS ¹⁹ 0.5

Ajidew ^R N 50 2.0

D-panthenol 1.0

Perfume oil q.s.

Water ad 100

¹⁸ An aqueous solution of

N, N-dimethyl-N- (2-hydroxyhexadecyl-1) -N- (2-hydroxyethyl) ammonium chloride

(approx. 27% active substance in water) (HENKEL)

1 ⁹ collagen hydrolyzate (protein content: 30%); CTFA name: Hydrolyzed

Animal Protein (GERMAN GELATINE FACTORIES STOESS & CO)

2.4.a. Corrugated foam

% By weight

Thioglycolic acid 8.0

Ammonia (25%) 6.3

Ammonium carbonate 3.0

Texapon ^R N 25 3.8

Cremophor ^R RH 60 5.8

Trilon ^R AS 0.3

Cutina ^R HR 20 1.0

Drivosol ^R 3.5 ^2l 3.5

Perfume oil q.s.

Water ad 100

²⁰ hardened castor oil; CTFA name: Hydrogenated Castor Oil (HENKEL)

²¹ propane-isobutane-butane-dimethyl ether mixture (24: 72: 3: 1) (HÜLS)

2.4.b. Fixing foam

% By weight

Potassium bromate 3.5

Texapon ^R N 25 2.0

Cutfna ^R HR 3.5

Dehydol ^R LS3 ²² 3.0

Lexein ^R X-250 ²³ 1.0

Ajidew ^R N 50 1.0

D-panthenol 1.0

Drivosol ^R 3.5 3.5

Perfume oil q.s.

Water ad 100 2 C _12-14 fatty alcohol + 3 ethylene oxide: CTFA name: Laureth-3 (Henkel) ²³ preserved protein hydrolyzate (NAARDEN)

2.5.a. Wellotion

% By weight

Thioglycolic acid 8.0

Ammonia (25%) 6.4

Ammonium carbonate 3.0

Lamepon ^R S ²⁴ 3.0

Merquat ^R 100 ²⁵ 0.2

Merquat ^R 550 ²⁶ 0.2

Disponil ^R SML-120-special ²⁷ 3.0

Perfume oil q.s.

Water ad 100

²⁴ protein hydrolyzate fatty acid condensate potassium salt; CTFA name:

Potassium Coco-Hydrolyzed Animal Collagen (approx. 30% active substance) (CHEMISCHE FABRIK GRÜNAU)

²⁵ poly (dimethyldiallylammoniumchloride); CTFA name: Polyquaternium 6 (MERCK)

²⁶ dimethyldiallylammonium chloride-acrylamide copolymer; CTFA name:

Quaternium 41 (MERCK)

²⁷ polyoxyethylene (20) sorbitan monolautrate (HENKEL)

2.5.b. Fixed distance

% By weight

Hydrogen peroxide (50%) 6.0

Cutina ^R HR 4.0

Keltrol ^R 0.1

Sodium hydroxide solution (45%) 0.8

Kerasol ^R 0.5 Ajidew ^R N 50 2.5

D-panthenol 0.5

Polymer JR ^R -400 ²⁸ 0.5

Perfume oil q.s.

Water ad 100

²⁸ quaternized hydroxyethyl cellulose (UNION CARBIDE)

2.6. Rinsing (between reducing and oxidizing step)

% By weight

Ajidew ^R N 50 2.0

Kelzan ^R 29 0.5

Cremophor ^R RH 40 ³⁰ 0.4

Perfume oil q.s.

Water ad 100

29 xanthan gum (KELC0)

30 hydrogenated castor oil, reacted with 45 moles of ethylene oxide per mole of castor oil (BASF)

2.7. Rinsing after oxidizing step)

Steno1 ^R 1618 ³¹ 2.0

Cremophqr ^R RH 40 0.4

Isopropyl palmitate / stearate 0.5

Dehyquart A ^R ³² 3.0

Glucose 1.0

D-panthenol 1.0

Merquat 550 1.0

Kelzan 0.6 Ajidew ^R N 50 2.0

Perfume oil, preservative, dye q.s.

Water ad 100 C16-18 fatty alcohol; CTFA name: Cetearyl Alcohol (HENKEL)

Trimethylhexadecylammonium chloride (25% active ingredient in water) (HENKEL)

Claims

P a t e n t a n s r u c h e

Process for the permanent shaping of hair, in which the hair is treated with the aqueous preparation of a keratin-reducing substance before and / or after a mechanical shaping, rinsed after an exposure time, then fixed with an aqueous preparation of an oxidizing agent and also rinsed after an exposure time, thereby characterized in that in at least one of the aqueous preparations and / or at least one of the rinses a compound (A) of the general formula (I).

in which at least one of the substituents R ¹ to R ³ represents a group -COOR ⁴ , in which R ^{4 is} hydrogen, an alkali metal ion, an alkaline earth metal ion or an ammonium ion ⁺ NHR ⁵ R ⁶ R ⁷ , in which R ⁵ to R ^{7 are} independent of one another Hydrogen, alkyl groups with 1 to 22 carbon atoms, hydroxyalkyl groups with 1 to 4 carbon atoms, alkenyl groups with 2 to 22 carbon atoms, acyl groups with 2 to 22 carbon atoms or optionally substituted aromatic groups with 6 to

10 are C atoms, and the remaining substituents R ¹ to R ^{3 are} hydrogen or alkyl groups having 1 to 4 C atoms, and at least one further compound (B) selected from the group consisting of panthenol, derivatives of panthenol, Includes allantoin, silicone oils and protein hydrolyzates.

2. The method according to claim 1, characterized in that the compounds (A) and (B) are contained in the aqueous preparation of the keratin-reducing substance and / or the aqueous preparation of the oxidizing agent.

3. The method according to any one of claims 1 or 2, characterized in that the compound (A) is contained in the aqueous preparation of the oxidizing agent.

4. The method according to any one of claims 1 to 3, characterized in that the compound (A) is 2-pyrrolidone-5-carboxylic acid or a salt of this acid.

5. The method according to claim 4, characterized in that the compound (A) is the sodium salt of 2-pyrrolidone-5-carboxylic acid.

6. The method according to any one of claims 1 to 5, characterized in that the compound (B) is selected from panthenol, allantoin and protein hydrolyzates.

7. The method according to claim 6, characterized in that the compound (B) is panthenol.

8. The method according to any one of claims 1 to 7, characterized in that the compound (A) in amounts of 0.1 to 20 wt .-%, in particular from 0.1 to 5 wt .-%, each based on the total amount preparation or rinsing.

9. The method according to any one of claims 1 to 8, characterized in that the compound (B) in amounts of 0.1 to 10 wt .-%, in particular from 0.1 to 5 wt .-%, each based on the total amount of Preparation or rinse is included.