DE2546951A1 - HAIR DETERGENT - Google Patents

Description

Patent attorneys Dipl.-Ing. F. Wexck \ <ann,

Dipl.-Ing. H. Weickmann, D1PL.-PHYS. Dr. K. Fincke Dipl.-Ing. F. A. Weickmann, Dipl.-Chem. B. Huber

H / KR / ZB _{g MONCHEN g6> DEN}

PO Box 860 820

MÖHLSTRASSE 22, CALL NUMBER 98 39 21/22

Reckitt & Colman Products Limited, London, England

Shampoos

[Addition to patent. ... ... (patent application P 23 53 860.5)]

Subject of the main patent. ... ... (P 23 53 860.5) is a cosmetic shampoo that contains at least one detergent and at least one additive to improve the Properties of the hair dispersed in an aqueous medium, which is characterized in that it contains as a detergent a sulfated fatty acid amine, amide or alkanolamide or a sulfated ethoxylated fatty acid amine, amide or alkanolamide with an average Ethoxy group content of 0 to 15 per mole and the carbon chains of the fatty acid residue each being 8 contain up to 18 carbon atoms or a salt thereof and as an additive to improve the properties of the hair, a compound that contains one or more cationic charges, has a backbone chain with at least 8 carbon atoms and a molecular weight above 200, and the pH of the composition being above 4 and below the pH at which the cationic charge

609818/1096

the additive to improve the properties of the hair becomes ineffective in the medium (cf. DT-OS 23 53 860). The present invention now relates to a further development of a such shampoo containing an improver additive.

Various combinations of detergents and additives have been used to improve the properties of the hair proposed to provide single phase liquid shampoos that both cleanse human hair as well as improve. The need for satisfactory liquid shampoos are among the many requirements However, doing enough has made such attempts difficult to succeed.

The properties that such liquid agents desirably have are that they should clean the hair, give a foam that in the presence of Fat is stable, but can be removed by rinsing the hair with water, the hair is shiny and pleasant Impart grip, have adequate storage stability and that they improve the properties of the hair.

The term "improvement in the properties of the hair" as used herein means an improvement the manageability of the hair, which is achieved when one or more of the following results are obtained:

(a) an improvement in the combability of "wet" and "dry" rinsed hair;

(b) an increase in the softness of the hair to the touch;

(c) a reduction in the tendency of the hair to become matted;

6098 18/1096

(d) a reduction in static electricity on the hair; and

(e) a noticeable increase in gloss.

It has now been found that a single phase improver system on the basis of a detergent can be obtained by using a cationic improver, namely a Polymer of an imine such as ethyleneimine or an alkyleneimine or an alkoxylated derivative of such a polymer with a special class of detergents combined.

The invention therefore relates to a shampoo which is characterized in that it contains at least one detergent from the group sulfated aliphatic amines, amides or Alkanolamides and sulfated ethoxylated aliphatic amines, amides or alkanolamides with a medium ethoxy group content per molecule of up to 15, the carbon chain of the aliphatic part containing 8 to 18 carbon atoms, and at least one imine polymer or an alkoxylated derivative of such a polymer in an aqueous medium contains.

The detergents used in the shampoos of the invention amine-based have a real amphoteric nature, while the amide and alkanolamide based detergents have lower anionic character at each pH than conventional anionic detergents.

The detergents which are derived from the amine, amide, alkanolamide or from alkoxylated derivatives thereof can according to Sulphation or sulphation processes are produced. In general, a sulfamation reaction is z. B. using sulfamic acid or an alkyl sulfamic acid, for the manufacture of amine-based detergents

609818/1096

more suitable than for the manufacture of detergents Amide or alkanolamide base. This is due to, that the milder sulphamation reaction has a more general utility, especially the amines, of which the detergents derived, are more labile bases than the corresponding amides or alkanolamides. The detergents based on amide and alkanolamide can by a sulfation reaction, e.g. B. using sulfur trioxide or chlorosulfonic acid, getting produced. However, under suitable reaction conditions, any reaction will work on all starting materials applicable.

The amine-based detergents used in the shampoos according to the invention can generally be represented by the formulas

D TvTU (nil PXJ Γ \ ^ Cn V ίτ \

K - JNn - ^ tilpUllpUjv 5UjA V-L ^

or ₂

R ¹ - N - (CH ₂ CH ₂ O) _b SO ₃ X (II)

12th

in which R, R and R independently of one another are an alkyl or alkenyl group having 8 to 18 carbon atoms mean; b is 0 or an integer from 1 to 15; and X is a hydrogen atom, an ammonium or quaternary ammonium cation or an ion of an alkali metal or alkaline earth metal. Preferably contain the

1 ?
Groups R, R and R each have 12 to 14 carbon atoms,

1 2
where the groups R and R in formula II can be identical or different.

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Examples of typical reactions that can be used to make the amine-based detergents, are the following implementations:

(1) R- NH ₂ + HSO ₃ NH ₂ >> R-NH- SO ₃

(2) R-NH - "(CH ₂ CH ₂ O) ₁₃ H + HSO ₃ NH ₂

R-NH- (CH ₂ CH ₂ O) _b SO ~ NHj R ²
(3) R ¹ - N - (CH ₂ CH ₂ O) _b H + HSO ₃ NH ₂

R ²
R ¹ - N -

Of course, when using an alkyl-substituted sulfamic acid instead of sulfamic acid, an amine salt can be used instead an ammonium salt can be obtained. The alkali metal and alkaline earth metal salts can, for example be prepared by a cation exchange by reacting a suitable ammonium salt with a strong base. Thus, the sodium salt can be obtained by treating the ammonium salt with sodium hydroxide.

The detergents based on amide and alkanolamide used in the shampoos according to the invention can generally can be represented by the following formulas:

R - CO - NH (Y) _n - (CH ₉ CH ₉ OkSO ^ X (Hl)

or

(Y) _a - (CH ₂ CH ₂ O) ₀ SO ₃ X

R-CON (IV)

(Y) _a - (CH ₂ CH ₂ O) _d SO ₃ X

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In this, R denotes an alkyl or alkenyl group with 8 to 18 carbon atoms, b is 0 or an integer from 1 to 15, X stands for a hydrogen atom, an ammonium or qua ternary ammonium cation or the ion of an alkali or alkaline earth metal, Y stands for a straight-chain or branched alkoxy group having 2 or more carbon atoms, a is 0 or 1, c is an integer from 1 to 14, d is is an integer from 1 to 14 and the sum of c and d is not greater than 15.

The group R preferably contains 12 to 14 carbon atoms,

Examples of typical reactions used to make the amide and alkanolamide based detergents are the following implementations:

(4) R - CONHCH ₂ CH ₂ OH + SO ₃ > R - CONHCH ₂ CH ₂ OS0 ₃ H

NH ₃

(5) RC0NHCH ₂ CH ₂ 0 (CH ₂ CH ₂ 0) _b H + SO ₃ »product

NaOH

CH

RCONHCH ₀ CH ₀ O (CH ₀ Ch ₀ O) ₁ SO - ⁺

(6) RC0NHCH ₂ CH0 (CH ₂ CH ₂ 0) _b H + HSO ₃ NH ₂

CH,

RC0NI-ICH _o CH0 (CH ₀ CH ₀ O), SO,

(CH ₀ CH ₀ O) H.
I ^ ^ ^c

RCO-N + ClSO ₇ H * product

(CH ₂ CH ₂ O) _d H ^{J JNaOH}

(CH ₂ CH ₂ O) ₀ SO ₃ Na ⁺

RCO-N

609818/10 9 6 (CH ₂ CH ₂ O) _d so3Na ⁺

-7- 2öA69b1

The conversion to the sulfated detergent can occur in the obi-

gen implementation may be incomplete. The percent conversion is usually in the range of 50 to 100 percent. If an alkanolamide is used as the starting material, there is no need to remove unreacted starting material since the unreacted alkanolamide in the shampoo acts as a foam stabilizer.

The chain length of the aliphatic part of the detergent preferably corresponds to that in the natural oils Coconut oil and palm kernel oil are found; d. H. the chain has mainly a chain length of 12 carbon atoms. However, the starting materials can also be of synthetic origin.

The ethoxy group content of detergents based on ethoxylated Amines, amides and alkanolamides, which are used in the invention Shampoo are included, can be up to 15 ethoxylate units per mole. Preferably however, detergents with an average ethoxy group content of 1 to 6 units per mole are used used. The desired average content of ethoxy groups can be obtained by adding two or mixed several detergents with different ethoxylate chain lengths.

The total detergent content in the shampoos according to the invention can be varied according to the desired degree of foaming and rinsing. Generally it is in the range from 5 to 35, preferably 10 to 30% by weight of the total composition. The detergent based on amine, amide or alkanolamide can be replaced in part by a further detergent, such a further detergent preferably less than 50 % of the total

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detergent matters. More detergents used

are amphoteric detergents, such as alkyl betaines, z. B. lauryl betaines, amide oxides such as alkyldimethylamine oxide and imidazolines, or anionic detergents such as salts of lauryl ether sulfate, e.g. B. the sodium or monoisopropanolamine salt.

The structure of the imine polymers used in the shampoos according to the invention is described as follows (J. Soc. Cos. Chem. 2-3, 593-603 (1972)):

- CH

R-CH

'N-

I J

-CH - CH - NH

r3

CH - CH -NK

In this, m is a value from 1 to 1500, preferably

"5 4
5 to 100, and R and R each represent a Η atom or an alkyl group having 1 to 6 carbon atoms. These products can generally be prepared by polymerizing an imine of the formula

R-

H-C

C-H

H ■

getting produced. In practice, there is considerable branching in the polymerization of the imines and in that Molecule there are primary, secondary and tertiary nitrogen atoms. The imine polymers can by reaction be alkoxylated with an alkylene oxide.

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The cationic character of the imine polymer increases as the acidity of the medium in which they are placed increases. In the above article it was described that at pH values of 8.0, 6.0 and 4.0, 25 %, 33 % and 50 % of the nitrogen atoms of the polyethyleneimine have a positive charge.

Examples of ethylene imine polymers available from Dow Chemical Co (Midland Mich. 48640) are the following products:

trademark

PEI 6 polyethyleneimine MG 600

PEI 12 polyethyleneimine MG 1200

PEI 18 polyethyleneimine MG 1800

PEI 600 polyethyleneimine MG 60,000

PEI 600 E polyethyleneimine MG 60,000

(reacted with ethylene oxide in a ratio of 1: 0.75).

The imine polymer used as a cationic enhancing agent is used, can in the shampoos according to the invention in an amount of active ingredient of 0.05 to 2.5 wt .-% of the total composition, preferably 0.1 to 1.0% by weight, can be used.

Cationic enhancers are noun for human hair, presumably due to an electrostatic one Attraction is due. When using the agents according to the invention, the improver is as thin continuous film adsorbed on the hair, whereby an improving effect is achieved on the hair. By adsorbing the cationic improver

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by this mechanism there is a whole or almost all of the covering Get each hair with a thin film of the enhancer. The film from the enhancer can be as thin as a monolayer and still have an enhancing effect on the hair.

In addition to the improvement effect, the polyethyleneimine shows a strong antimicrobial effect against several Organisms. In particular, it has been shown that polyethyleneimine has a powerful inhibitory effect against the organism P. ovale which has been reported to accompany scaling. Other antimicrobial Agents such as 2,4,4'-trichloro-2-hydroxy-diphenyl ether (irgasan DP 300 - Ciba-Geigy), trichlorocarbanilide, cetyltrimethylammonium chloride, benzalkonium chloride, heavy metal salts of 2-pyridine thiol-1-oxide or colloidal sulfur can be added to the shampoos according to the invention.

Polyethyleneimine has a strong chelating effect and it forms complexes with some compounds, the metal ions included, such as B. the heavy metal salts of 2-pyridine thiol-1-oxide (Pyrithione). So is z. B. the zinc salt of pyrithione hardly soluble in water, but forms a complex of zinc pyrithione with excess polyethyleneimine (MW 600) · a clear aqueous solution that is used in the shampoos according to the invention is soluble, resulting in a clear shampoo that does not come off when centrifuged Separate solid substances. The preferred heavy metal salt of pyrithione is the zinc salt and those of the invention Shampoos can contain up to 0.5% by weight of this salt. Other suitable heavy metal salts are z. B. cobalt, manganese and nickel salts.

The preferred pH of the shampoo depends on the particular Wording off. An increase in pH increases

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the cationic character of the shampoo. Accordingly the preferred pH of the compositions is as low as possible, provided that the resulting mixture contains the shows the required stability and that it meets the normal safety requirements for shampoos. Of the The pH of polyethyleneimine-containing agents which do not contain zinc pyrithione is preferably in the range of 4 to 10. The preferred pH of the agent, however, will vary according to the molecular weight of the one used Polyethyleneimine. If for example a polyethyleneimine low molecular weight such as PEI 6 is used then the preferred pH range is 5 to 7. In the case of longer-chain polymers such as PEI 600 and the alkoxylated ones For longer-chain polymers such as PEI 600 E, the preferred pH range is 7 to 9.

For agents that contain the zinc pyrithione / polyethyleneimine complex is also included, the preferred pH is within the limits of product stability and Safety as low as possible and it is generally in the range from 4 to 10. The pH value at which in suitably clear homogeneous mixtures can be obtained, however, depends inter alia on the detergent system used in these blends. In agents in which the sodium salt of a sulfated, with 1.9 mol ethoxylated coconut fatty acid monoethanol amides and coconut dimethylbetaine detergents are used, the preferred pH range is 8.5 to 9, while for agents in which use a detergent mixture containing the ammonium salt of sulfated coconut, the sodium salt of sulfated, with 6 moles of ethoxylated kbkosamine and coconut dimethyl betaine the preferred pH range is 5-7.

The pH of the agent can be adjusted to the required value by adding an acid, preferably phosphoric acid, hydrochloric acid,

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Acetic acid, sulfuric acid, tartaric acid, and. Citric acid or can be adjusted by adding a base such as sodium hydroxide, triethanolamine or monoisopropanolamine.

Other cationic improvers can include those according to the invention Shampoo in amounts of 0.1 to 10% by weight, preferably 0.1 to 2.5% by weight, based on the total composition, be incorporated. The additional cationic enhancing agents can be mono- or polycationic Be compounds or mixtures thereof.

Examples of monocationic compounds in the inventive Means that can be used are the following substances:

Alkyltrimethylammonium halides,

N-alkyl pyridine halides,

N-alkyl-isochino.linium halides,

Dialkyldimethylammonium halides,

Alk2? Laryldimethylammonium halides, fatty acid aminoalkylamines, sold under the trademark

Sapamine, and
Alkylbenzyl hydroxyethyl imidazolinium chloride.

Mixtures of such compounds can also be used. To. The solubility of such monocationic Compounds can improve the nitrogen groups be ethoxylated. This is particularly important in the case of dialkyl quaternary ammonium salts, their solubility is low in aqueous medium.

Examples of typical polycationic compounds that can be used in the agents according to the invention, are the following substances:

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High molecular weight aminoethyl acrylate / phosphate / acrylate copolymers sold under the trademark CATREX (previously known as RESYN 78-3510), National Adhesives Limited, quaternized vinyl pyrrolidone copolymers sold under the trademark GAFQUAT, e.g. B. GAE ¹ QUAT 734, 755, 750 or 759 from GAF Limited,

low molecular weight condensation products of adipic acid, dietarylrylene triamine polyamide and epichlprhydrin sold under the trademark DELSETTE, e.g. B. DELSETTE 101 or 201 from Hercules Limited, and

cellulose ethers containing quaternary nitrogen sold under the trademark POLYMER JR by Union Carbide Corporation. Mixtures of such compounds can also be used (RESYN, CATREX, GAFQUAT, DELSETTE and POLYMER JR are trademarks).

The shampoos according to the invention can contain additives that are used for current shampoos are common provided that these additives reduce the adsorption mechanism of the cationic improver on the hair do not interfere to a significant extent and that they interfere with the effectiveness of any antimicrobial agent does not decrease significantly.

In the inventive shampoo non-ionosphere may generate foam stabilizers are incorporated, which are typically used in such shampoo formulations. Typical examples of foam stabilizers are amine oxides such as kbkosdimethylamine oxide, alky! Betaines such as coconut dimethyl betaine, alkanolamides such as monoethanolamide and diethanolamide of coconut fatty acids or their ethoxylated derivatives. The foam stabilizers are generally incorporated into the compositions according to the invention in amounts of 1 to 5% by weight, based on the total weight of the mixture as a whole.

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Also thickeners, for example simple salts of ethoxylated fatty acids or thinners such as glycols, polyglycols or Polyalkylene glycols can be used in the agents according to the invention be incorporated.

Other additives such as protein hydrolysates, lanolin and its derivatives, plant or balsam extracts, vitamins, Vegetable oils, dyes, perfumes and preservatives such as formalin or dodecylguanidine can be incorporated, without the basic properties of the agents being impaired.

Pearlizing or matting agents can also be added, such as ethylene glycol monostearate, Ethyl Glycol Distearate. Alkaline earth salts or fatty acid alcohols.

The invention is illustrated in the examples. Unless otherwise stated, all percentages are on based on weight.

example 1

The following materials were used at room temperature in one

Mixing vessel mixed together: .... _

° / o Weight / weight

Sodium salt of sulphated coconut fatty acid monoethanolamide etholyzed with 1.9 mol of the formula
RCONHCH ₂ CH ₂ O (CH ₂ CH ₂ O) _{1 3} Na 9To 65.0

(30 % - ± ge aqueous solution) (a)

Coconut fatty acid diethanolamide 2.0

Coconut dimethyl amide oxide

(30% aqueous solution) 4.0

Polyethyleneimine MW 600 0.3

Formaldehyde 0.1

Dye, flavoring agent, sodium chloride as far erfor _w 609818/1096 sary

Water _{to 100 #}

The pH of the mixture was adjusted to 5 »2 by adding citric acid. It became a clear liquid shampoo obtain.

(a) The conversion to sulfate in the preparation of this detergent was 75 % effective so that the 30 % aqueous solution contains 24 % sulfate and 6 % unreacted coconut fatty acid monoethanolamide ethoxylated with 1.9 moles.

Example 2

The following materials were used at room temperature in one

Mixing vessels mixed together:

% Weight / weight

Sodium salt of sulfated coconut amine, ethoxylated with 6 moles, of the formula RNH (CHpCH ₂ O) ₆ SO ₃ Na (30 % aqueous solution) (b;

Coconut fatty acid diethanolamide Coconut dimethyl betaine (30% aqueous Solution)

Polyethyleneimine MW 600

Preservative, coloring, aromatic

sizing agent, sodium chloride if necessary

Water to 100.

The pH of the mixture was adjusted by adding citric acid set to 5.5. A clear liquid shampoo was obtained.

(b) The conversion to this detergent was done with an efficiency of 75 % -

Example 3

The following materials were used at room temperature in one

Mixing vessel mixed together:

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60, 0 3, 5 2, 0 0, 25th

Sodium salt of sulfated, with 1.9 mol ethoxylated coconut fatty acid monoethanolamide (30 % - ± ge aqueous
Solution) (as in example 1)

4.5 moles of ethoxylated coconut fatty acid monoethanolamide

Coconut dimethylamine oxide (30 % aqueous solution)

Polyethyleneimine MW 60,000,

with ethylene oxide in a ratio of 1: 0.75

implemented

Preservative, color, salt, flavoring agent

water

% Weight / weight

70.0

2.5 4.0

0.4

if necessary to 100.

The pH of this mixture was raised with citric acid 8.2 set. A clear liquid shampoo was obtained.

The shampoos prepared in Examples 1, 2 and 3 were compared to an additive for improvement compared the properties of the hair-containing shampoos, each with one half of the head treated and the uncombed hair after. last rinsing process was visually compared. The one with the means of the head halves treated in Examples 1, 2 or 3 appeared as if they had been combed through while the halves of the head that had been treated with the comparison agent were visibly matted. It was found, that the hair has a significantly better wet and dry combability through the shampoos according to the invention and that matting was practically prevented. Furthermore, that was with the invention Medium washed hair clean and it showed a soft feel and good shine. --.- -

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Example 4

% Gewient / Gewient

Ammonium salt of sulfated

Coconut amine of formula

RNH.SO ₃ NH ₄ (50 % paste) 15.0

Sodium salt of sulfated,
with 6 moles of ethoxylated coconut amine (30 % solution) as in Example 2 45.0

Coconut fatty acid diethanolamide. 3.0

Coconut dimethylamine oxide (30%

Solution) 6.0

Polyethyleneimine (MW 600) 0.13

Flavoring agent, color,

Preservatives etc. where necessary

Water rest.

The pH of the agent was adjusted to 5.3 with citric acid set and a clear liquid shampoo was obtained.

Example 5

In the preparation of the following agent, Irgasan DP 300 and coconut fatty acid diethanolamide were mixed together and it was heated until a clear solution was obtained. The remaining components were then put into mixed into a mixing vessel at room temperature.

% Weight / weight

Sodium salt of sulfate with

1.9 moles of ethoxylated coconut oil

acid monoethanolamide (30%

aqueous solution) as in Example 1 65.0

Coconut fatty acid diethanolamide 3.5

809818 / 109S

Coconut dimethyl amide oxide (30% solution) CATREX RESIN (20 % aqueous solution) sodium chloride polyethyleneimine (MW 600) 2,4,4'-trichloro-2-hydroxyphenyl ether (irgasan DP 300) formalin dyes, flavoring agent water

% Weight / weight

3.3

5.0 2.0 0.5

0.15 0.15

if necessary to 100.

The pH of the agent was adjusted to 5.3 with citric acid and a clear liquid shampoo was obtained.

The preparation was examined for bacteriostatic activity. The following results were the average get minimal inhibition dilution:

Average minimum inhibition and thinning

Example 5

Example 5 without Irgasan

Example 5 without PEI 6

Staph. aureus 1 in 1500

1 in 1 in

E. coli
in 1600

in 5
in 2000

P. oval 1 in 3200

1 in 1600 1 in

These results describe the specific and powerful inhibitory activity of PEI 6 against P. ovale, an Or-

60981 8/1096

ganism associated with dandruff. Irgasan DP has only weak activity against this organism, but a combination of the two substances results in a very strong one Broad spectrum antimicrobial activity.

Another bacteriological test was performed to test substantivity. A slice of calf skin was soaked in a dilute solution of the shampoo at 37 ^° C. for 5 minutes. It was then removed, rinsed thoroughly, placed on an agar plate and incubated. The zones of inhibition were measured in mm. The following results were obtained:

Staph. aureus P. ovale

(Dilution 1 in 10) (dilution 1 in 4) 45 mm 18 mm

These values confirm the antimicrobial anti-bust activity Active ingredient of this mixture.

Example 6

In making the following agent, the zinc pyrithione was used mixed with the PEI 6 and some water. The resulting clear solution was then mixed with the remaining ingredients mixed in a simple mixer:

% Weight / weight

Sodium salt of sulfated, with

1.9 mol ethoxylated coconut fatty acid

ren-monoethanolamide (30% aqueous

Solution) as in Example 1 65.0

Coconut dimethyl betaine

(30% aqueous solution) 10.0

POLYMER JR 400 ⁺⁺ 0.2

Zinc pyrithione O> 25

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% Weight / weight

Polyethyleneimine (MW 600) 0.47

Colorants, flavoring agents, preservatives as far as necessary

Water . to 100.

Polymer JR 400 is a polycationic polymer from Union Carbide.

The pH was adjusted to 8.6 with hydrochloric acid.

The resulting shampoo was a clear mixture that evolved during storage or after prolonged centrifugation do not separate particulate matter.

This product was tested for bacteriostatic activity in a manner similar to Example 5. There were get the following results:

sr

Average minimum inhibition dilution

Staph. aureus E. coli P. ovale 1 in 800 1 in 315 1 in 2400

Zone of inhibition of the calf skin in mm

Staph. aureus P. ovale (dilution 1 in 10) (dilution 1 in 4) 20 mm 16 mm

These results show a strong inhibitory effect against P. ovale and a high degree of substantivity.

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The agent of Example 6 was examined for its effectiveness against dandruff in a test group of 24 people. A group of four skilled observers were employed to visually assess the degree of dandruff in subjects each week before shampooing and to record the degree of severity on an arbitrary scale. A control hair washing agent was used during the first five weeks of the experiment, after which the hair washing agent of Example 6 was used for the next 10 weeks. The reduction in the extent of flaking was pronounced with the agent of Example 6 and it reached a maximum after 8 weeks of treatment with it. The reduction in dandruff was greater than that found in a parallel test which had been carried out under similar conditions with a commercially available zinc pyrithione shampoo. This commercially available shampoo contained four times the zinc pyrithione content (1 %) in suspension form.

Example 7

In a manner similar to the agent of Example 6, the following agent was prepared:

% Weight / weight

Sulfated sodium salt, with

1.9 mol ethoxylated coconut fatty acid

ren-monoethanolamide (30% aqueous

Solution) as in Example 1 45.0

Coconut dimethyl betaine

(30% aqueous solution) 10.0

TEXAPON IES ⁺⁺ 10.0

Zinc pyrithione 0.25

Polyethyleneimine (MW 600) 0.47

Sodium chloride 3.0

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% Weight / weight

Colorings, flavoring agents, preservatives as far as necessary -

V / ater to 100.

A commercially available anionic wetting agent from Henkel Ltd., which contains the alkanolamine salt of fatty alcohol ether sulfate at a nominal content of 60 % active detergent.

The pH of the agent was adjusted to 8.55 with hydrochloric acid. The resulting shampoo was clear Mixture from which no particulate matter is deposited during storage or after long periods of centrifugation.

The product was tested for bacteriostatic activity as in Example 5.

The following results were obtained:

Average minimum inhibition dilution

Staph. aureus E. coli P. ovale 1 in 3200-6400 1 in 800 1 in 3200-6400

Zone of inhibition of the calf skin in mm

Staph. aureus P. ovale ——

(1 in 10 dilution) (1 in 4 dilution) 24 mm 17 mm

Example 8

In a manner similar to the agent of Example 6, the following agent was prepared:

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% Weight / weight

Sodium salt of sulfated, with

6 mol ethoxylated coconut amine (30 % -

ige solution) as in Example 2 60.0

Ammonium salt of sulfated

Coconut amine (50% paste) like

in Example 4, 20.0

Coconut dimethyl betaine (30% aqueous solution; 5.0

Zinc pyrithione 0.25

Polyethyleneimine (MW 600) 0.47

Flavoring agents, coloring agents, etc. if required Water to 100.

The pH of the agent was adjusted to 6.4 with citric acid. The resulting liquid shampoo was clear.

Examples 9-11

Three compositions were prepared containing the ingredients listed below.

Weight%

Ex. 9 Ex. 10 Ex.

Sodium salt of sulfated, with 1.9 mol ethoxylated Kok οsmonoäthanolamid like
in example 1 55 55 55

ο osdimethyl betaine
(30 % solution) 12.50 12.50 12.50

Monoisopropylamine salt

of 2 moles of lauryl ether sulfate

(28 % active) 16.50 16.50 16.50

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Monoisopropanolamine lauryl sulfate (35 % active) Monoisopropanolamine zinc pyrithione Polyethyleneimine (MW 600) Polyethyleneimine (MW 1200) Polyethyleneimine (MW 1800)

Colorants, aromatizing agents

water

Ex . 1 254695 1 Example 9 4, 40 0 ex. 11 1
4.40 3, 00 4.40 3.00 0, 25th 3.00 0.25 0.25 0.44

so far
required

to 100

0.50

so far
required

0.75

as far as required.

to 100 on

The compositions of Examples 9 to 11 were prepared in a manner similar to Example 6.

The pH of these exemplary mixtures was adjusted to 8.7 with sulfuric acid. All mixes yielded clear shampoos which were tested for bacteriostatic activity as in Example 5. There were get the following results:

Average minimum inhibition dilution

Example 9. Example 10 Example 11

Staph. aureus

1 in 1600 1 in 1 in

E. coli

in 800
in 400
in 400

P. ovale

1 in 2000 1 in 2000 1 in 2000

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Inhibition zone of the calf skin in mm

9 Staph. aureus E. coli P. ovale example 10 23 20th , 5 16 example 11 21 20th 16 example 12th 20.5 19th 16 example

A shampoo was made,. "where the desired average length of the ethoxylate chain in the ethoxylated amine sulfate detergents obtained in the manner was that two detergents with different lengths of ethoxylate chains were mixed.

The shampoo contains the following ingredients:

% Weight / weight

Sodium salt of sulfated, with

10 mol ethoxylated coconut amine (50 % -

solution) (c) 45.0

Sodium salt of a sulphated coconut amine ethoxylated with 15 mol (50 % solution) (c) 6.0

Coconut dimethyl betaine (30% solution) 10.0

Polyethyleneimine (MW 1800) '0.6

TEXAPON IES (as in Example 7) 15.0

Flavoring agents, coloring agents, if necessary, water to 100.

(c) The conversion of these detergents to the sulfate was 70 % effective.

The ingredients were in a simple mixer at room temperature mixed up.

609818/1096

The pH of the agent was determined by adding sulfuric acid set to 7.1.

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Claims (11)

Patent claim back 1. Shampoo containing at least one detergent and one cationic improver in an aqueous medium, according to patent (P 23 53 860.5), characterized in that it is a sulfated detergent aliphatic amine, amide or alkanolamide or a sulfated ethoxylated aliphatic amine, amide or alkanolamide with an average content of ethoxy groups of up to 15 per mole, the carbon chain of the aliphatic part contains 8 to 18 carbon atoms and that it is an imine polymer as a cationic improver or contains an alkoxylated derivative of such a polymer. 2. Shampoo according to claim 1, characterized in that it has an amine-based detergent as the detergent the formula R-NH- (CH ₂ CH ₂ O) _b S0 ₃ X or ο R ^ R ¹ - N - 1 2
wherein R, R and R are independently an alkyl or alkenyl group having 8 to 18 carbon atoms, b is 0 or an integer from 1 to 15, and X is a hydrogen atom, an ammonium or quaternary ammonium cation or the ion of an alkali metal or Alkaline earth metal contains. 609818/1096 3. Shampoo according to claim \, characterized in that it is a detergent based on amide or alkanolamide with the formula R-CO-NH (Y) _a - R-CON wherein R is an alkyl or alkenyl group having 8 to 18 carbon atoms, b is 0 or an integer of 1 to 15, X is a hydrogen atom, an ammonium or quaternary ammonium cation or the ion of an alkali or alkaline earth metal, Y is a straight-chain or branched alkoxy group having 2 or more carbon atoms denotes, a is 0 or 1, c is an integer from 1 to and d is an integer from 1 to 14, where the sum of c and d is not greater than 15 contains ·. 4. Shampoo according to one of the preceding claims characterized in that the mean length of the ethoxylate chain of the detergent is 1 to 6 units per Moles. 5. Shampoo according to one of the preceding claims, characterized in that the mean length of the ethoxylate chain of the detergent is obtained in such a way that one mixes two or more detergents in different lengths of the ethoxylate chain. 6. Shampoo according to one of the preceding claims, 609818/1096 characterized in that it additionally contains a further detergent, the proportion of the further detergent is less than 50% by weight of the total amount of detergent. 7. Shampoo according to one of the preceding claims, characterized in that the imine polymer is a polymerization product of an imine of the formula I I H-C - C-H wherein R and R independently of one another are a hydrogen atom or denotes an alkyl group having 1 to 6 carbon atoms and wherein the degree of polymerization is 1 to 1500, is. 8. Shampoo according to claim 7, characterized in that the degree of polymerization of the imine polymer is 5 to 100 is. 9. Shampoo according to one of the preceding claims, characterized in that the imine polymer or its alkoxylated derivative is present in an amount of 0.05 to 2.5 % by weight of the total mixture. 10. Shampoo according to one of the preceding claims, characterized in that the imine polymer in complex with a heavy metal salt of 2-pyridinthiol-1-oxide is present. 11. Shampoo according to one of the preceding claims, characterized in that there is another cationic improver in an amount of 0.1 to 10% by weight of the Total mix contains. 609818/1096