DE2207477A1 - Foaming agents activated by monoalcohols - Google Patents

Description

j. "; .- !. ·: ν., wc": - 'Γ .'Λ.ί Γ'.ϋ,; . ": ■ du.; ■■. ΛΓνί.».:.; ^R O! \ C. Lü '. ·: ;;

Munich, February 17, 1972 M / 11808

L 'O R E A L' 14, Rue Royale, Paris, France

Foaming agents activated by monoalcohols

The present invention relates to foaming cosmetic products Preparations, and in particular shampoos and foam baths, based on the surface-active substances defined below Compounds whose foam properties are improved by the presence of one or more monoalcohols.

209837/1226

Μ / 11808 Ζ

The surfactants useful in the present invention Compounds contain at least one nitrogen atom that is directly or indirectly attached to the fatty chain, whereby this nitrogen atom is positively charged or by adding an inorganic or organic acid or by quaternization can be positively charged according to known methods, and / or a positively charged sulfur atom. «··

Cationic surfactants fall under this definition Compounds such as the amines, the amine oxides, their salts, their quaternization products, the sulfonium compounds, the amphoteric and zwitterionic surfactants Links.

The presence of the monoalcohols not only improves the foam properties but also the detergent properties the surface-active compounds mentioned, and makes it easier to comb washed hair, both when it is damp like after drying.

These monoalcohols are neither water soluble nor foaming and the improvement they bring about in those mentioned Agent is therefore based on a synergistic effect.

(A) Cationic surfactants

The cationic surfactants that can be used in the compositions of the invention are:

(1) Compounds that essentially consist of a fatty chain attached directly or indirectly to a nitrogen atom is bound, which is in the molecule in the form of the free base,

if such a molecule is soluble in water, or as an amine oxide, or as a salt thereof with inorganic or

2 0 9 8 "3 ⁷ I Π 2 2 6

M / 11808 3

organic acids or as quaternization products, the can be obtained by known methods.

(2) sulfonium compounds

The compounds (I) can be amine, amine oxide, or quaternary ammonium. They also contain sulfonium groups.
(I) amine compounds

(a) Compounds whose lipophilic chain attaches directly to the nitrogen atom can be bound, as in formula (I)

(D

wherein R is an alkyl, alkenyl or alkylaryl radical, derived from natural animal or vegetable fatty acids, or of synthetic origin, for example derived from olefins, which can comprise 10 to 24 carbon atoms, wherein the alkyl chains and alkenyl chains can be straight-chain or branched, or mixtures such radicals, and in which R- ^ and R ₂ , which can be the same or different, a monovalent element or a monovalent radical, such as a hydrogen atom, a methyl, ethyl, phenyl, hydroxyethyl, polyethoxyhydroxyethyl, hydroxypropyl, Dihydroxypropyl radical, where R- and Rp together with the nitrogen atom to which they are bonded can form a heterocycle which can also contain an oxygen atom or another nitrogen atom and thus form a heterocyclic amine such as pyrrolidine, morpholine or piperidine.

- 3 209837/1226

M / 11808 7

(b) compounds whose lipophilic chain to the end nitrogen atom is bound by means of a chain of atoms which, in addition to the carbon and hydrogen atoms, have one or may comprise several atoms, such as nitrogen, oxygen or sulfur atoms.

These connections can be made, for example

-by condensation of polyamines with alkyl halides, or by cyano-ethylation of fatty amines followed by one catalytic hydrogenation,

-by cyanoethylation of fatty alcohols. or by condensation secondary amines with epoxides with a fatty chain or with corresponding halohydrins, for example, are compounds the formula

RO- [C ₂ HjO-CCH ₂ OH)] _n -CH ₂ -CHO H-N

^X R ₂

wherein R, R- ^ and R2 have the meanings given for formula (i) have, η represents a statistical mean value from 0.5 to and

[C ₂ H ₃ O- (CH ₂ OH)] one of the two isomers

-CH ₂ -CH-O- and -CH-CH ₂ O-OH ₂ OH CH ₂ OH

means that according to French patent 1,538 can be produced, usable according to the invention,

- 4 209837/1 226

j - by condensation of mercaptans with secondary amines in the presence of formaldehyde, or by condensation of mercaptans with tertiary amines with an epoxy function, or also from secondary amines with halohydrins with thio-

I ether function,

^! - by condensation of fatty acids or their chlorides with! Dialkylaminoethanols or with oxyäthylenisiert dialkyl, aminoethanols, or by condensation of secondary ι amines and epichlorohydrin with a sodium or potassium ■ soap according to French patent 1 313 143,

i - tertiary primary-by condensation of fatty acids from corresponding _f chlorides or esters with amines such as \ dimethyl or Diäthylaminoäthyl- or propylamine, or with secondary-tertiary amines.

(c) Alkyl imidazoline compounds of the formula (III)

N CH ₂

Il I ■■ you)

R-C CH «

NO"

wherein R has the meaning given for formula (i), R ^{1 is} a hydrogen atom or a monovalent radical, such as

-CH ₂ -CH ₂ OH

-CH ₂ -CH ₂ -NH ₂ or

- 5 '-209837/1226

h / 11808 Τ 22Ö7477

; ■ ^ CH ₂ -CH ₂ OH

! -CH ₂ -CH ₂ -N

CH ₂ -CH ₂ OH

can mean.

! (II) amine oxide compounds

J These compounds are obtained from those described above

j tertiary bases by classical methods, for example

j by oxidation with hydrogen peroxide, optionally in

I presence of a lower organic acid such as acetic acid.

: Form in compounds with an intermediate thioether function i amine oxides with sufficient amounts of hydrogen peroxide

I 1

! with sulfoxide or sulfon function.

I ■. .

i The amine compounds described are in the form of salts

i inorganic acids such as hydrobromic acid, hydrogen chloride acid, sulfuric acid, phosphoric acid or of salts or- "

I ganic acids, such as acetic acid, lactic acid, citric acid, Tartaric acid, p-toluenesulfonic acid, salicylic acid, or in

! Form of free bases, if these compounds are water-soluble, can be used.

(ill) Quaternary ammonium compounds

These compounds can be obtained through

- Quaternization of aliphatic or aryl-aliphatic tertiary amines and in particular dimethylated fatty amines

- 6 209837/1226

M / 11808. f

: by known methods, for example with the help of connections, such as methyl iodide, methyl bromide, methyl chloride, Ethyl chloride, ethyl bromide or ethyl iodide, benzyl chloride or bromide, dimethyl sulfate, an alkyl mesylate or -tosylate, chloroacetamide, glycol or glycerol chlorohydrin,

• ethylene oxide, propylene oxide, glycidol,

- Quaternization of aromatic or heterocyclic amines, -like Pyridine, 2-, 3- and 4-picoline, quinoline, the N-alkylmorpholines, etc. with alkyl halides with a fatty chain, and preferably with alkyl bromides or with alkyl mesylates or tosylates,

- O-alkylation of amine oxides with the help of ethyl or Methyl iodide, bromide or chloride, dimethyl sulfate or else Alkyl mesylates or tosylates. In the case of tertiary amines or amine oxides with a thioether function, quaternary ones are obtained

\ Sulfonium compounds.

I (2) sulfonium compounds

These compounds can be prepared from the corresponding thioethers using quaternization procedures similar to those described above getting produced.

(B) Amphoteric and zwitterionic betaine compounds

These compounds can be easily prepared by known methods such as

- Condensation of halogen-alkane-carboxylic acids and essentially Chloric or bromoacetic acid or propionic acid with primary, secondary or tertiary fatty amines or else due to the action of halogenated diacids, such as chlorosuccinic acid, on the same amines,

- 7 209837/1226

M / 11808 ■ © ■

- Condensation of amino acids tni-b alkyl halides, with

chloromethyl ethers derived from higher alcohols, or with epoxies with a fatty chain,

- Condensation of primary, secondary or tertiary amines, including heterocyclic amines, such as Pyridine, with oc-halogenated fatty acids,

- Addition of primary or secondary fatty amines to acidic compounds with activated double bonds, such as acrylic acid or acids derived from maleic acid monoamide according to French patent specification 1 ~ bkk 212,

- Condensation of halogen-alkane-carboxylic acids, such as chloroacetic acid, with alkyl thioethers, for example dodecyl methyl sulfide, one can obtain a nitrogen-free ampholyte compound of the sulfonium carboxylic acid type, which is also according to the invention is usable.

Mono alcohols

The monoalcohols which can be used as synergistic agents are saturated straight-chain aliphatic alcohols of natural or synthetic origin with 10, 12 and 1h carbon atoms, ie i-decanol, 1-dodecanol, 1-tetradecanol or mixtures thereof.

These monoalcohols used in the present invention The role of the synergistic agent is played by non-foaming, water-insoluble compounds in quantities from 1 to 80% by weight and preferably from 5 to 30% by weight, based on the weight of the surface-active compounds mentioned, can be used.

209837/1226

M / 11808

The foaming agents according to the invention can be in the form of liquids, creams, pastes, gels or powders. They can also be conditioned in aerosol form.

These agents can contain one or more of the aforesaid cationic, amphoteric and zwitterionic surfactants Contain agents, with certain cationic agents acting as germicides.

In addition to the surface-active agents mentioned, the foaming agents according to the invention can also contain other surface-active agents Surface-active compounds, such as non-ionic compounds, contain the presence of which the described synergistic Effect does not diminish.

As non-ionic compounds used in the invention foaming agents can be included, for example, the following can be mentioned:

the condensation products of ethylene oxide and fatty alcohols,

the mercaptans with a long chain, for example with 10 to carbon atoms,

the alkylphenols, such as octylphenol, nonylphenol and dodecylphenol,

the compounds of the formula

RO- [C ₂ H ₃ O- (CH ₂ OH)] _n -H

wherein R is a straight-chain or branched alkyl or alkenyl radical having 8 to 22 carbon atoms or one

- 9 -209837/1226

Μ / 11808 10

Alkylaryl radical having 8 to 22 carbon atoms, in which the straight-chain or branched alkyl chain has 2 to 16 carbon atoms may contain, or a hydrocarbon radical derived from alcohols produced by hydrogenation of lanolin or from natural waxes, such as beeswax, from resin acids or cyclic fatty acids, means, and where η represents a statistical mean value and an integer or decimal number can be equal to or less than 10,

the compounds of the formula

RO- [C ₂ H ₃ O- (CH ₂ OCH ₂ -CHOh-CH ₂ OH)] _n -H

wherein R is a straight-chain or branched alkyl or alkenyl radical having 8 to 22 carbon atoms, which is optionally Includes hydroxyl groups and intermediate groups in which heteroatoms means and η represents a statistical mean value which is an integer or a decimal number is equal to or less than 5,

the compounds of the formula R-CH-CH ₂ -O- [C ₂ H ₃ O (X)] -H

0 [C ₂ H ₃ O (X)] _q -H

wherein R is a straight-chain or branched hydrocarbon radical with 8 to 22 carbon atoms, which optionally comprises hydroxyl groups and intermediate groups in which heteroatoms are contained, X is a group CH ₂ OH or CH ₂ OCH ₂ -CHOH-Ch ₂ OH, ρ and q represent statistical mean values that can be whole numbers or decimal numbers equal to or less than 10, where the sum (p + q) is equal to or greater than 1 and less than or equal to 10 ,

- 10 209837/1226

M / 11808. ^ '

the compounds of the formula

RS- [CH ₉ -CHOH-CH ₉ -O] -H 0

wherein R represents a straight-chain or branched alkyl, alkenyl or hydroxyalkyl group with 8 to 22 carbon atoms, a cycloaliphatic or arylaliphatic group having 8 to 22 · carbon atoms or a mixture of said R _e ste, η a mean statistical value greater than l'and equal or less than 10,

the compounds of the formula

R-CHOH-CH ₂ -O- [CH ₂ -CHOH-CH ₂ O] _n -H

wherein R is an aliphatic, cycloaliphatic or arylaliphatic A radical having 7 to 21 carbon atoms or a mixture of such radicals, the aliphatic chains can be saturated or unsaturated, straight-chain or branched and oxygen and / or sulfur atoms and can in particular include ether, thioether and / or hydroxymethylene groups, and η denotes the middle Indicates the degree of polymerization and is an integer or decimal number greater than 1 and equal to or less than 10,

the compounds of the formula

RO

CH - CHO

- H

wherein R is a straight-chain or branched alkyl radical 8 to 30 carbon atoms or an alkylaryl radical

- 11 -

209837/1226

with 12 to 40 carbon atoms, or an alkyl-polyalkylenoxy radical with 14 to 60 carbon atoms and 1 to 10 oxygen atoms or a cycloaliphatic radical with 10 to 30 carbon atoms, means one of the symbols A and B is a hydrogen atom and the other is a group of the formula CHpZ , wherein Z is a ^ alkylthio radical of the formula R ¹ S or alkylsulfonyl radical of the formula R ¹ S-, wherein

R ¹ denotes an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms, and η is an integer between 1 and 20.

The agents according to the invention can also usually Ingredients and auxiliaries used in cosmetics contain the appearance, the color, the smell, the Viscosity, pH and any other specific property desired. You can also use perfumes, thickeners and contain dyes. '

The perfume content of the shampoos is 0.1 to 1% by weight and preferably 0.2 to 0.6% by weight and that for bubble baths 1 to 10% by weight and preferably 2 to 6% by weight, based on the total weight of the agent.

These foaming agents can be used for various industrial Applications are used. A particularly interesting form of application are the means for cosmetic use, like shampoos, bubble baths, etc.

The foaming agents have a pH between 2.5 and 10.5 and preferably between 3 and 9.5 for shampoos and between 6 and 8 for foam baths.

- 12 -

209837/1226

M / 11808 7 *

The addition of alcohols to the surface-active agents mentioned changes the foam properties, the detergent properties, the treatment properties as well as the appearance of the foam of the foaming agents concerned are considerable.

The following advantages result:

- A very significant improvement in the onset of foam, faster onset of foam formation, immediate foam formation,

- a strong increase in foam power,

- An improvement in the appearance of the foam, which is slightly denser, is more consistent, creamier and therefore more pleasant to the touch, probably giving it these properties through a better water retention can be imparted.

- The stability of the foam is also increased.

- These properties remain in the presence of greasy Soiling, for example in shampoos, is obtained, which also improves the detergent properties the means.

It is also observed that both damp and dried hair are easier to comb. The hair is also more pleasant and softer to the touch, without becoming heavier. The inclusion of monoalcohols in shampoos brings about a substantial improvement in the quality of the shampoo, both in terms of the foam, the detergency and the 'Treatment effect is concerned.

The content of monoalcohols in the shampoo agents is 0.4 to 4.5% by weight and preferably 0.6 to 4% by weight , based on the total weight of the agent.

In the foam baths, the content of monoalcohols is 1 to 10% by weight and preferably 1.5 to 5% by weight , based on the total weight of the agent.

- 13 209837/1226

The content of cationic, amphoteric and / or zwitterionic surfactants is in the Shampoo agents 0.5 to 30 wt .-% and preferably 3 to 25% by weight, based on the total weight of the agent.

In the case of foam baths, this percentage is the same as that mentioned surfactants 10 to 80% by weight and preferably 20 to 60% by weight, based on the total weight of the agent.

The improvement of the foam in terms of volume, stability and creaminess can be achieved with the help of Ross and Miles Apparatus are shown, the rapid and well reproducible measurements, on the one hand of the volume of the foam and its Stability and on the other hand the water retention allowed.

The results obtained with the various products, those without addition and in the presence of various Amounts of synergistic agents expressed as a percentage based on the weight of the anhydrous surfactant The means tested are summarized in tables.

Likewise, for surfactant concentrations of 5%, 2%, and 0.5%, the foam heights are in cm at time zero (1) and after 5 minutes (2) and the water volumes retained in the foam at time zero are given in ml.

The synergistic agents used are the mixture of synthetic decanol, dodecanol and tetradecanol, the is sold under the trade name "Alfol 10-12", the synthetic dodecanol and the synthetic tetradecanol, which are sold under the trade names "Alfol 12" and "Alfol 14" by CONDEA PETROCHEMIE GESELLSCHAFT, Hamburg will.

- 14 -

209837/1226

M / 11808. ™

The composition of "Alfol 10-12" is as follows:

Decanol 85.0 + 4 % dodecanol 8.5 + 2 % tetradecanol 6.5 + 2 %

All measurements are carried out with tap water having a hardness of 34 ° (French degrees of water hardness), and a thermostat! Catalyzed temperature of 35 ⁰ C, which temperature corresponds to a practical use.

The pH reported for each of the surfactants tested is that of a 5% mother liquor contained in is divided into two parts, one serving as a control without the addition and the other adding the desired amount of alcohol will. The pH was adjusted with either lactic acid or sodium hydroxide in all cases.

- 15 209837/1226

- N

(CH ₂ -CH ₂ O) _x -H (CH ₂ -CH ₂ O) -H

χ + y =

Foam height in cm Ethomeen C 25

(Armor Dial Inc. Chicago, U..S.A.)

pH 4 water retention in ml

Alcohols ro ο co J Without alcohol

^ 'Dodecanol

% 5% o

12th

2 ° / oo 0.5 ° / o% o 2 ° / oo 0.5 ° / oo

0 14.5 8 13 6 8.5 5% 21.5 17.5 18 14.5 13 30
60

20 50

10 30

C ₁₁ H ₂₃ -COO-CH ₂ -CH ₂ -N

C ₂ H ₅ pH 3.5

Without alcohol 0 18th 12th 18th 5 7th , 5 6th Dodecanol 10% 21st 13th 19 14th , 5 1

40
50

40 40

R - CO- [O-CH ₂ -CH ₂ ] _n - N

C ₂ H ₅

C ₂ H ₅

R = alkyl radical derived from coconut fatty acids η. = 2.5 pH 3.5

Alcohols

Without alcohol dodecanol

Foam height "in cm

5 % o 1

0 15 5 % 18

KJ RO- [C ₉ H, O- (CH ₀ OH)] -CH ₀ -CHOH-CH, -N

, C ₂ H ₄ OH

₀ OH)] -CH ₉ CHOHCH ₄ N

η = 0.5 R = mixture of dodecyl and tetradecyl Water retention in ml

2 ° / 00 2 0, 5 %O 5 %O 2% o 0.5 per cent 1 6th 1 2 13th 10 '3 - 40 30th - 16 5 - 40 40 5

[C ₂ H ₃ O- (CH ₂ OH)] means -CH ₂ -CU-O-

CH ₀ OH or -CH-CH ₂ -O-

pH 4

Without alcohol dodecanol

0 18 Ib 18.5 16 9.5 10 % 21.5 18 20.5 17 13.5 15.5 36 50

36 50

16 K 30 <=>

RO- [C ₂ H ₃ O- (CH ₂ OH) I _n -CH ₂ -CHOH-CH ₂ -N

CH ₃ C ₂ H ₄ OH

η = 0.5 R = mixture of dodecyl and tetradecyl

SO ₄ CH ₃

pH 4

Alcohols

Foam height in cm

Water retention in ml

/ oo

2 per cent

0.5%> 5%

2 per cent, 0.5 per cent

Without alcohol
Dodecanol O
5% 17.5
21 17th
21.5. 15th
18th 15th
19th 12.5
15.5 12.5
16 10
12th 15th
18th 13th
15th , 5 30th
60 40
50 30:
40; CH ₃
RN> O
CH ₃ R: Laury1 Ammonyx LO
(Onyx Chemical Co. jersey City, New
pH 4 Jersey, U.S.A.) | Without alcohol
Dodecanol O
10% - 17th
20th 14th
18th 16
21 13.5
..18 16
16.5 3
12th ■ 20th
40 20th
40 .30. j
40 I. ppH 8 > ⁵ ! Without alcohol
Dodecanol O
10% 4th
17th 16
19th , 5 3
15.5 , 5 20th
30th '20
40 ' 30!
40 I.

H
VD • CH ₃ + % Br "
Foam height in cm 16 2 2 per cent 2 0.5 ° 15th 12th 13th / oo pH 8
Water retention in 40 2 "° / oo ml • 30th 11808 / oo I. C ₁₄ H ₂₉ - N - CK ₃
CH ₃ 5% o 20th 14th 1 13th 1 18.5 16 15th 2 5 per cent 50 0.5 ° 50 Alcohols O 1 19.5 21st 15.5 20th 11 18.5 15th 14.5 9 50 24 5 % 15.5 21st 23 15th 18th 15th 11 12.5 20th 60 80 Without alcohol Cl " 24.5 19th Alkyl radical derived from 17th 14.5 13th 80 60 pH 3 30th Dodecanol R = Tallow fatty acids 40 2091 "? ^H 3
RN - CH ₂ -CH ₂ OH O ■ ' 13.5 30th 40 CO L ^CH 3; J 5% ■ 17.5 11 40 50 _ _v Without alcohol 5 ^c / o 16.5 12th 60 40 IO Alfol 10-12 1055 17.5 12th 50 CD Dodecanol 5% 16.5 8th 50 11 Tetradecanol

rv> ο

t J

R - N CH-

Cl "

R = hybrid of dodecyl and hexadecyl

Catigene T 80, Industrie Chimique de Voreppe (France) ^

pH 7

Foam height in cm

Water retention in ml

Alcohols ' % 5 ° / oo 2 2 ° / oo IV) 0.5 O 5 / oo , 5 5 per cent 2 per cent 0.5 per cent 1 11 1 8.5 1 Ul 2 , 5 Without alcohol 0 . 17th 15.5 14th , 5 14th 11 7th 30th 25th 20th Dodecanol 5% 18th 14th 16 , 5 14th 12, 9 30th 30th 30th 10% 17th 17th , 5 12, 9 30th 40 30th

N- (CH ₂ ) _{i: r} CH ₃

Br "

Isothane Q 15

(Onyx Chemical Co. Jersey City, New Jersey, U.S.A.)

pH 7

Without alcohol 0 14th 5 10 5 14th 10 5 10 5 , 5 20th 20th 20th Dodecanol 5% 20, 17, 19th 15, 15th 12th 4O ₁ : 40 40

• M / 11808

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209837/1226

I. I.
I. 0 /
f—
CH ₃ J
I. % ₂ -CH ₂ OH L. %O 2 in cm / oo 2 7th 0.5 ° / oo 2 pH 3.5
Water retention in * pH 2.5 2% o ml , 5 ^c O
00 7oo to
ro
ο IV)
IV) Alcohols o: L2 2 ° _ 12th 1 _ 5 per cent 20th 0 ο: 5% : LS ₁ 5 14.5 1 5 12.5 1 3 40 20th 0 ro Without alcohol 5% : 9 6th 20th 40 20th co
CX) Dodecanol - CH SO ₃ ~
Foam height SO ₄ CH ₃ " 16, - 50 37 / Γ 5 L5 , 5 5 3 1226 L8 15th 6th 2 10 10 Cn pHpc "* S - CH
OH, 10 4th 40 10 Without alcohol 15th Dodecanol

CH

- CHOH - CH ₂ - N

CH,

pH 4

Foam height in cm

Water retention in ml

I. Alcohols % - O 5 %O 2 1 7oo 2 0, 5% o 5 ° / oo 2 , 5 14.5 16 13th 30th %O 0.5 ° / oo • δ: K) O ■ ul
I. 10% 1 : 0 2 0 1 2 17th 16 13.5 50 207477 CO
CO
CO Without alcohol O 2 , 5 14 15th 10 2 0 -J Dodecano.l 5% 17th 1 - 40 40 0 1226 CH ₃
R ~ ⁺ N - CH ₅ -COO = Mixture Empigen BN
Albright &
Whltehaven, Wilson, Marchon Division,
Cumberland, England CH ₃ R. 16.5 of dodecyl and tetradecyl pH 4
* , 5 Without alcohol 18th 18th 16: 20th 30th Dodecanol 21st 21st 50 40

R-CONH- (CH ₂ ;

CH ₃ ^L N CH ₂ COO '

R = lauryl

Foam height in cm

Tego Betaine L7
(Goldschmidt) pH k

Water retention in ml

Alcohols R-N ^ CH ₂ -CH ₂ ° / o 5 ° / oo 2 2 ° / oo 2 ui 0.5 9 O / oo 2 5% o 2 ° / oo 0.5 ° 20th / oo Without alcohol 1 1 1 20th ISJ Dodecanol 14th 13th pH 10, CD
CO Without alcohol 0 17th 16 15th 15th 13th 10, , 5 10 5 30 30th 30th ⁰⁰ I.
co
-JI \) Dodecanol 5% 20th R = 19th 15th 7th , 5 50 40 40 4 -
/ 1 22 CH ₂ -CH ₂ -COONa Lauryl Deriphat 160 cn - , 5 (General Mills, Minneapolis, U. -COONa , 5 15 5 13 7th 0 18th 15th 16, 13th 5 2, 40 40 5% 21st 18th 5 50 40

ro ro ο

^ CR,

CH OH

CH ₂ -CH ₂ O-CH ₂ -COONa

CH ₂ -COONa

Foam height in cm

Miranol C ₂ M

(Miranol Chemical Co, New Jersey, U.S.A.)

pH 8.4

Water retention in ml

(V) Alcohols CH ₂ - % 5 O / oo 2 - N 17th 2 ° H / oo 2 0.5 O / oo 5 11 ° / oo 2 ° / oo 0.5 per cent o5f Coconut fatty acids VJl
I. R-NH-CH - 1 16.5 18.5 1 15.5 1 2 12th ΙΌ
CD Without alcohol Without alcohol O 18th , 5 17.5 20th 18th ^H 5 15th 14, 5 11.5 15th 40 40 40 30th (O Dodecanol Alfol 10-12 5% 21st 16.5 16 18th 18th 5 14.5 14th 11 9 50 50 40 50 co. Dodecanol 10% 20th 17, 21st 10 6.5 60 60 20 { 60 i Tetradecanol Cp 21st : 30:
... - fO 16 IO CONH- (C. . R. - Alkyl radical derived from co COOH 14.5 pH 3.5 0 19th , 5 17th 13, 5 40 40 5% 21st , 5 18.5 16 60, ' 60 5% 23 14th 16 70 70 5% 19th 11 60 50

CH,

S ~ \

CH ₂ - CONH- (CH ₂ ;

R t

CH ₂ COONa

Cl

R = alkyl radical derived from coconut fatty acids

pH 8

CD (D GO ι alcohols

Foam height in cm

5 ° / οο 1 water retention in ml

2% o

0.5% ο 1 '2

Without alcohol

Dodecanol 10%

14 - 12.5 -

19 15.5 16.5 14 11.5 8.5

30 40

30 40

700 2 per cent. 0.5 per cent

20 30

M / 11808

j Example applications for shampoos

Example 1 The following means are made:

Cl "

RN- CH ₂ - CH ₂ OH

Ip - VaHqV

R = alkyl radical derived from tallow fatty acids

Lauryl alcohol

Lactic acid as much as needed for

Water as much as needed for

6 g

0.6 g pH 5

100 g

The result is an agent that is significantly more foaming and a little more active washing than without lauryl alcohol. As a shampoo When used, this agent results in a consistent and stable foam. ■.

Example 2

R -

CH,

N - CH ₂ - CH ₂ OH

CH-

Cl "

5 g

R = alkyl radical, derived from tallow fatty acids «C ₁₂ H ₂₅ - 0 - [C ₂ H ₃ O- (CH ₂ OH) J ₄ ^ ₂ - H

5 g

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! Synthetic lauryl alcohol from Condea

sold under the trade name "Alfol 12" 1 g

Lactic acid as much as required for pH k

Water as much as necessary for 100 g

A clear agent that is one and a half times more foaming than without lauryl alcohol. The detergent properties are clear improved, the foam is also denser and more stable.

Example 3

CH,

N-CH

CH,

■ χ.

Br "

10 g

CH ₀

t * - S— »0

CH ₂ -CHOH-CH ₂ OH

5 g

1.5

R = mixture of dodecyl and tetradecyl

Synthetic lauryl alcohol sold by Condea under the trade name "Alfol 12" 0.5 g

Lactic acid as much as needed for

Water as much as needed for

pH 3 100 g.

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\ Μ / 11808

Example 4

R - NH - CH - COOH C ₃ H ₅

CH ₂ - CONH - (CH ₂ ) ₃ - N '10 g

C ₂ H ₅

»Μ ¹

R = alkyl radical derived from coconut fatty acids

Lauryl alcohol 1 g

Lactic acid as much as needed for pH

Water as much as necessary for 100 g

The volume and stability of the foam in this shampoo are significantly greater than those of the corresponding cationic ones Solution.

If the pH is adjusted to 8.5 with triethanolamine, the foam is similar to that obtained at pH 5.

Example 5

R - NH - CH - COOH ""

, ^ L ₂ H ₅

CH ₂ - CONH - (CH ₂ ) ₃ - N '7g

R = hydrocarbon chain derived from coconut fatty acids

CH ₃ R - N - CH ;, - CHpOH

CH ₃

Cl "3 g

R = alkyl radical derived from tallow fatty acids.

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Ί2 ^η 25

- S O

CH ₂ - CHQH - CH ₂ O

-H 5g

2.5

Synthetic Lauryl Alcohol, under the trade name "Alfol 12" sells 1.5 g

Lactic acid as much as necessary for * "pH 5,

Water as much as necessary for 100 g

The volume and stability of the foam in this shampoo are significantly greater than those of the corresponding cationic ones Solution.

Example 6

■ ■ ···· ■■■■ · ι

CH ₂ - CH ₂ - COONa

R-N ^, 10 g

^: CH ₂ - CH ₂ - COONa! R = lauryl

Lauryl alcohol, oxyethylene with 12 mol ^ ethylene oxide 10 g '

'Lauryl alcohol 3 g i

ι NaOH as much as necessary for pH 8.5

Water as much as necessary for 100 g

The remedy is practically twice as foaming as in its absence! of lauryl alcohol. '

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Example- 7

The following coloring shampoo is produced ":

Sodium N-lauryl-3-imino-dipropionate 10.0 g

Lauryl alcohol with 12 moles of ethyl enoxide 10.0 g

Lauryl alcohol,> 3.0 g

Coconut fat diethanolamide 4.0 g

Ammonia with 22 ° Be 10 ml

Dyes

Resorcinol

m-aminophenol base p-aminophenol base p-Ni tro-p-phenylenediamine p-tolylenediamine

Hydroquinone ₍

Ethylenediaminetetraacetic acid sodium bisulfite D = 1.32 Water as much as needed for

Mix 50 g in a plastic applicator
the above formulation with the same amount of hydrogen peroxide in 20 volumes and apply the mixture to the hair with the applicator or with a brush.
Distribute by massaging until there is ample foam. You wait 30 minutes, then you rinse and dry. A golden blonde shade is obtained on a light brown background.

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0.040 G 0.060 G 0.280 G 0.022 G 0.110 G 0.170 G 3 G 0.800 ml 100 g

209837/1226

Example 8 , bubble bath

One prepares the following composition for one Foam bath is intended:

N CH ₉ ti ι ^ -

C ₁₁ Hp - CN - CHp - CHp - 0 - CHpCOONa 60 g

XX d-3 * .HH H

OH CH ₂ COONa

Lauryl alcohol, oxyethylene with 12 mol

Ethylene oxide 12 g

Lauryl alcohol 5 g

Lactic acid as much as required for pH 6.5

Water as much as necessary for 100 g

This results in a very concentrated foaming agent that is practically twice as foaming as without lauryl alcohol.

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Example 9

The following shampoo is made:

R-NH-CH-COOH _Q

CH ₂ -CONH-C CH ₂ ) ₃ -N - 8 g

^ C ₂ H ₅ ...

R. = alkyl radical derived from coconut fatty acids Containing alcohol having 12 to 14 carbon atoms

70 % dodecanol and 30 % tetradecanol 1 g

Lactic acid as much as necessary for pH 5

Water as much as necessary for 100 g

If you adjust the pH to 8 with triethanolamine, then the Foam similar to that obtained at pH 5.

Example 10

The following shampoo is made:

R-NH-CH-COOH

CH ₂

- CONH -CCH ₂ ) ₃ - N 10 g

R = alkyl radical derived from coconut fatty acids

Lauryl alcohol-myristyl alcohol 50:50 Ig

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Perfume . 0.4 g

Lactic acid, as much as necessary for pH 5

Water as much as necessary for 100 g

The volume and stability of the foam in this shampoo are significantly greater than those of the corresponding cationic ones Solution.

If the pH is adjusted to 8.5 with triethanolamine, then the Foam similar to that obtained at pH 5.

Example 11 The following shampoo is prepared:

R - NH - CH - COOH _n "

.C ₂ H ₅

CH ₂ - CONH - (CH ₂ ) ₃ - N '7g

R = alkyl radical derived from coconut fatty acids.

CH, ⁺

RN-CH ₀ -CHoOH

Cl "" ^ 3 g

R = alkyl radical, derived from tallow fatty acids

S - CH ₂ - CHOH - CH ₂ O

₂ - CHOH - CH ₂

2.5

-H 5 g

Myristyl alcohol 1.5 g

Perfume 0.4 g

Lactic acid, as much as necessary for pH 5

Water as much as necessary for 100 g

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The volume and stability of the foam in this shampoo are significantly greater than those of the corresponding cationic ones Solution.

Example 12

The following shampoo is made:

R - NH - CH - COOH
ι ■

CH

₂ - CONH - (CH ₂ ) ₃ - N 7g

R = alkyl radical, derived from coconut fatty acids

Lauryl alcohol, oxyethylene with 12 mol

Ethylene oxide 15 g

Decyl alcohol 2 g

Perfume . 0.5 g

Lactic acid, as much as necessary for pH 5

Water as much as necessary for 100 g

The volume and stability of the foam in this shampoo are significantly larger than without decyl alcohol.

Although it is not always stated, the funds contain
generally a sufficient amount of perfume in accordance with the above examples to make their use more attractive.

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209837/1226

The teaching of the present invention also includes the use of one or more monoalcohols of natural or synthetic origin, selected from decanol, dodecanol, tetradecanol and mixtures thereof, to improve the foam properties of foaming cosmetic agents which contain one or more surface-active agents which contain at least one nitrogen atom which is bound directly or indirectly to the fatty chain, this nitrogen atom being positively charged or being positively charged by adding an inorganic or organic acid or by quaternization, and / or containing a positively charged sulfur atom. The foaming cosmetic compositions improved in the manner according to the invention can also contain auxiliaries which ensure the properties of appearance, color, odor, viscosity, pH and other desired properties.

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209837/1226

Claims (1)

1. Foaming cosmetic agents that contain one or more surface-active agents, the at least one Contain nitrogen atom that is bound directly or indirectly to the fatty chain, this nitrogen atom being positive is charged or positively charged by adding an inorganic or organic acid or by quaternization can be, and / or contain a positively charged sulfur atom, characterized in that the foam properties by the presence of one or more monoalcohols of natural or synthetic origin chosen from Decanol, dodecanol and tetradecanol and mixtures thereof, are improved, these agents also containing auxiliaries that can affect the properties of appearance, color, smell, viscosity, pH and others ensure desired properties, t 2. Agent according to claim 1, characterized in that the surface-active agents are selected from cationic, amphoteric and zwitterionic surfactants. 3. Agent according to claim 2, characterized in that the cationic surface-active agent is in the form of the water-soluble free base is present. - 37 - 209837/1226 M / 11808 J. A. Agent according to claim 2, characterized in that the cationic surfactant is in the form of a inorganic or organic salt is present. 5. Composition according to claim 4, characterized in that it is a salt of hydrobromic acid, chlorine-r hydrofluoric acid, sulfuric acid, phosphoric acid, acetic acid, Lactic acid, citric acid, tartaric acid, p-toluenesulfonic acid or salicylic acid. 6. Composition according to claim 5, characterized in that the cationic surfactant is in the form of Hydrochloride, hydrobromide or lactate is present. 7. Composition according to claim 2, characterized in that the cationic surfactant is in the form of a quaternary ammonium compound is present. 8. Composition according to claim 1, characterized in that it is a shampoo or a foam bath. 9. Composition according to claim 1 to 8, characterized in that it has a pH between 2.5 and 10.5. - 38 - 209 837/122 6 M / 11808 ^ 10. Composition according to claim 2, characterized in that the amount of monoalcohols 5 Ms 30 wt .-%, based on the weight of the cationic, amphoteric and / or zwitterionic surfactants. 11. Composition according to claim 1, representing a hair shampoo, characterized in that it contains surfactants in an amount from 0.5 to 30% by weight and preferably from 3 to 25% by weight, based on the total weight of the agent, and as a synergistic agent for the foam 0.4 to 4.5% by weight, based on the total weight of the agent, 1-decanol, 1-dodecanol, 1-tetradecanol or mixtures thereof and optionally also perfume, dyes, thickeners, other surface-active agents Agents, especially non-ionic, surface-active agents Contains agents, as well as other auxiliaries commonly used in cosmetics, and a pH between 2.5 and 10.5 and preferably between 3 and 9.5. 12. Means according to claim 1, representing a foam bath, characterized in that it contains surfactants in an amount from 10 to 80% by weight and preferably from .. 20 to 60% by weight, based on the total weight of the agent, 1 to 10% by weight and preferably 2 to 6% by weight, based on on the total weight of the agent ^ 1-decanol, 1-dodecanol, 1-tetradecanol or mixtures thereof and possibly also other: in particular non-ionic surface-active agents, Contains perfume and other auxiliaries commonly used in cosmetics. 13. Means according to claim 1 to 12, characterized in that, that it is in the form of a liquid, cream, paste, gel, or powder. - 39 - 209837/1226 M / 11008 HO 1 Λ. Mi H.t.ol according to claims 1 to 13, by gokonnzoichnot, that it is in aerosol form. - / to - 209837/1 226