Note: Descriptions are shown in the official language in which they were submitted.
!
,
_________
What follows below after ~his bracketed nore, excep~ for the edge line nurnbers and
bottom page numbers, is a ~ransla~iotl in~o English of the Genn~n language origul~l
specifcationforPCTApplica~ionNo.PCT/EP92/02118.filedonSeptemberl6.1992;
HAIR TREATMENT PREPARATIONS
This invention relates to hair treatment preparations containing a combination of
a zwinerionic polymer and a pyrrolidone carboxylic acid.
Any cleaning or cosmetic treatment of the hair affects its natural structure. The
result of this is thati after such a treatment, for example washing, dyeing or permanent
5 waving, the hair often shows a number of unsatisfactory properties in addition to the de-
sired changes. Besides a deterioration in wet and dry combability. these unsatisfactory
properties include electrostatic charging and inadequate moisture retention. In many cases,
!
the curl retention capacity of the dry hair is also unsatisfactory. In addition, it is desirable
that the scalp remain largely unaffected by the treatment.
o To remedy the situation, corresponding components either bave to be added to the
hair treatment preparations, or the hair has to be subsequently subjected to a separate treat-
ment with substances which are normally formulaled as a rinse.
~.
2~?,~ 009
Polymeric compounds, more particularly cationic, anionic and zwitterionic poly-
mers, are often used as such substances to improve the proper~ies of h~ur. Corresponding
polymers are described, for example, in US 3,816,616, US 3,472,840, DE-A-21 50 557,
DE-A-28 17 369, DE-A-28 11 010, DE-A-33 nl 121, DE-A-30 44 738, DE-A-37 08 451,
5GB-B-2,11)4,091 and DE-A-39 29 973.
2-Pyrrolidone-5~arboxylic acid is a constituent of the so-called natural moisluriz-
ing factor ("NMF") of the skin. Accordingly~ this compound or its sodium salt is used as
a moisturizer for skin creams and o~her cosmetic products. In addition, it is known that
the salts increase the softness and elasticity of the horny layer and the surface of hair
~Qfibers (H.P. Fiedler, Lexikon der Hilfsstoffe f~r Pharmazie, Kosmeti~ und angrenzende
Gebiete lTitle in English: Dictionary of Auxiliary Substances for Pharmacy, Cosmetology,
and Adjoining Fieldsl, 3rd Edition, lEditio Canto Aulendorf, 1989~, pages 110, 111).
It has now been found that the effects of both classes of compounds in hair treat-
ment preparations are synergistically enhanced if these compounds are used in combina-
tion with one another. --
Accordingly, the present invention relates to preparations containing typical con- . ~:
stituents for the treatment of hair, characterized in that they contain a combination of
A) a zwitterionic polymer and
B) a compound corresponding to general formula (I): -
R 1 o : :
N
in which at least one of the substituents R' to R3 is a group -CooR4, where R4 is hy-
drogen, an aL~cali metal ion7 an aL~caline earth metal ion or an ammonium ion 'NHR5R6R7,
where R5 to R7 independently of one another represent hydrogen, aL~cyl groups having I
to 22 carbon atoms, hydroxyalkyl groups having I to 4 carbon atoms, aL~cenyl groups
having 2 to 22 carbon atoms, acyl groups having 2 to 22 carbon atorns or aromadcgroups, opdonally substituted, having 6 to 10 carbon atoms, and the remaining subsdtuents
Rl to R3 represent hydrogen or alkyl groups having I to 4 carbon atoms.
In the context of the invendon, zwitterionic polymers are polymers which cuntain
;~1<~
both cationic groups and anionic groups or groups readily convertible into such groups.
Cationic groups are, for examplet groups having at least one arnmonium or phos-
phonium unit. Examples of a group readily convenible into a cationic group are primary,
secondary and in particu!ar tertiary amino gr~ups. Ammonium groups are preferred cat-
5 ionic groups.
Suitable anionic groups are, for example, carboxylic acid, sulfonic acid and phos-
' phoric acid groups in free form or in salt form. The carboxylic acid groups and their al-
kali metal, aL~caline earth metal, aluminum and arnmonium salts are preferred anionic
groups.
The polymers used in accordance with the invention may be produced from mono-
mers having both cationic and anionic groups. In this case, the polymers may consist of
a single type of monomer. However, copolymers of the monomers mentioned and other
nonionic monorners may also be used. Such nonionic monomers may be, for example,vinyl-based esters and amides, such as methyl acrylate, ethyl acrylate, methyl methacryl-
! 15 ate, ethyl methacrylate, hydroxypropyl methacrylate and acrylamide. These copolyrners
preferably contain at least 20 % and, more preferably, at least 50 %, of ionic monomers.
Polymers preferably used in accordance with the invention are produced ~rom at
least two ionic monomers, a cationic monomer and an anionic monomer. Cationic and
anionic monomers may be present in a molar ratio of 1:1. However, monomers of one
20 type, more particularly the cationic monomers, are preferably used in excess. Cationic and
anionic monomers are generally used in a ratio of 95:5 to 60:40. ln addition, the poly-
mers may contain nonionic monomers of the type mentioned above in quantities of up to
50 mole-% and, more particularly, in quantities of up to 20 mole-%.
The zwitterionic polymers described in DE-A-39 29 973 are preferred for the pur-25 poses of the invention. These zwitterionic polymers are essentiaUy composed of
a) monomers having quaternary arnmonium groups corresponding to general formula
(11):
R3-CH=CR9-Co-Z-(CDH2n)-N(~?R'RI'R't A() (II),
in which R8 and R9 independently of one another represent hydrogen or a methyl
group and R~, R~ and Rl2 independently of one another represent alkyl groups
having I to 4 carbon atoms, Z is an NH group or an oxygen atom, n is an integer
of 2 to 5 and A(-) is the arion of an organic or inorgarlic acid
and
~1 B) monomeric carboxylic acids corresponding lo gen~ral formula (III):
:I R'3-CH=CR'4-CooH (III),
.¦ in which R'3 and R'4 independently of one another represent hydrogen or methyl
groups, or alkali me~al, alkaline earth metal, aluminum or ammonium salts of these
~ s acids.
-~ Suitable starting monomers for the monomers (o;) are, for example, dimethylan~ln-
¦ oethyl acrylarnide, dimethylaminoethyl methaclylarnide, dimethylaminopropyl acrylarnide,
dimethylaminopropyl methacrylamide and diethylarninoethyl acrylamide, where Z is an
NH group, or dimethylaminoethyl acrylate, dirmethylaminoethyl methacrylate and diethyl-
10 arninoethyl acrylate, where Z is an oxygen atom.
The monomers mentioned are prepared by known methods as described, for
example, in US 3,878,247, DF,-C-28 19 735, DE-C-28 36 520, DE-C-34 02 599 or CH
464 891.
The monomers containing a tertiary amino group are then qualernized in known
15 manner, methyl chloride, dimethyl sulfate or diethyl sulfate being particularly suitable al-
kylating agents. The quaternization reaction may be carried out in aqueous solution or in
a solvent. Suitable methods are described, for example, in DE-A-33 30 326, DE-A-25 37
378 and DE-A-32 44 274.
Monomers of formula (II) which are derivatives of acrylamide or methacrylarnide
20 are advantageously used. Monomers containing halide, methoxysulfate or ethoxysulfate
ions as counterions are also preferred, as are monomers collesponding to formula (II) in
which R~, R" and Rl2 are methyl groups.
Acrylamidopropyl trimethyl ammonium chloride is a most particularly preferred
monomer of formula (Il).
Monomeric carboxylic acids (B) are acrylic acid, methacrylic acid, crotonic acidand 2-methyl crotonic acid. Acrylic acid or methacrylic acid, more particularly acrylic
acid, is preferably used. Preferred salts of these carboxylic acids are the lithium, sodium,
potassium, magnesium, calcium and aluminum salts. The sodium salt is particularly pre-
ferred. The ammonium salts in which the ammonium ion may contain one to three alkyl
groups haviag I to 4 carbon atoms or hydroxyaL~cyl groups having 2 to 4 carbon atoms
as substituents may also be used. Salts containing unsubsdtuted ammonium ions and tri-
ethanolammonium ions are preferred.
So far as the preparation of these zwitterionic polymers is concerned, specific
2 ~ 2 ~
refer~nce is made to the disclosure of DE-A-39 29 973.
The compounds of general fortnula ~I) are derivatives of 2-pytrolidone.
Preferred deriva~ives are 2-pyrrolidone-3-, -4- and -5-carboxylic acid and saltsthereof. Preferred salts of these compounds are the sodium, potassium, calcium, magnes-
5 ium and ammonium salts, in which the arnmonium ion contains 1 to 3 Cl4 alkyl groupin addition to hydrogen.
Particularly preferred compounds of general forrnula (I) are 2-pyrrolidone-S-car-
boxylic acid and salts thereof. The sodium salt is most particularly prefetred.
The zwitterionic polymers are present in the preparations according to the inven-
10 tion in quantities of preferably 0.1 to 10 % by weight, based on the preparation as awhole~ Goncentrations of 0.2 to 5% by weight are patticularly preferred.The compounds corresponding to formula (I) are present in the preparations ac-
cording to the invention in quantities of preferably 0.1 to 15 % by weight and, more
preferably, 0.5 to 10 % by weight, based on the preparation as a whole.
In addition to the zwitterionic polymers and compounds corresponding to general
formula (I), the preparations according to the invention may contain any of the consti-
tuents typically encountered in hair treatment preparations. The nature of the preparation
determines which of the constituents mentioned in the following are present therein.
Most hair treatrnent preparations, such as shampoos, rinses, perrnanent wave lo-
20 tions, hair dyes and hair tints, are aqueous preparations containing surfactants. The sur-
factants used ate anionic, cationic, zwitterionic, arnphoteric and/or nonionic surfactants.
Anionic surfactants suitable for use in the hair treatment preparations according
to the invention are any of the anionic surfactants which are suitable for use on the human
body. They are characteriæd by a water-solubilizing anionic group, for example a carbox-
25 ylate, sulfate, sulfonate or phosphate group, and a lipophilic alkyl group having approxi-
mately 10 to 22 carbon atoms. Glycol or polyglycol ether groups, ester, ether and amide
groups and hydroxyl groups may also be present in the molecule. The following are ex-
amples of suitable anionic surfactants in the form of the sodium, potassium and arnmoni-
um salts and also the mono-, di- and trialkanolamrnonium salts having 2 or 3 carbon at-
30 oms in the aLtcanol group:
- linear fatty acids having 10 to 22 carbon atorns (soaps~,
- ether carboxylic acids corresponding to the ~ormula R-O-(CH2-CH20)~-CH~-
COOH, in which R is a linear aL~cyl group having 10 to 22 carbon atoms and x =
7J ~ f ~ ~3 3
O or I to 10,
- acyl sarcosides having 10 lo 18 carbon atoms in the acyl group,
- acyl taurides having 10 to 18 carbon atoms in the acyl group,
.1 - acyl isethionates having 10 to 18 carbon atoms in the acyl group,
s - sulfosuccinic acid mono- and dialkyl esters having 8 to 18 carbon atoms in the al- : -
. kyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters having 8 to 18 :
carbon atoms in the alkyl group and I to 6 oxyethyl groups,
. - linear alkane sulfonates having 12 to 18 carbon atorns, ..
- linear alpha-olefin sulfonates having 12 to 18 carbon atorns,
- alpha-sulfofatty acid methyl esters of f~ty acids having 12 to 18 carbon atoms,
~j - aL~cyl sulfates and aL~yl polyglycol ether sulfates corresponding to the formula R-
O(CH2-CH20),~-OSO3H, in which R is a preferably linear alkyl group having 10
. to 18 carbon atoms and x = O or I to 12,
- mix~ures of surface-active hydroxysulfonates according to DF.-A-37 25 030,
. 1S - sulfated hydroxyaL~cyl polyethylene and/or hydroxyaL~cylene propylene glycol ethers
according to DE-A-37 23 354,
. - sulfonates of unsaturated fatty acids having 12 to 24 carbon atorr~s and I to 6
double bonds according to DE-A-39 26 344,
- esters of tartaric acid and citric acid with alcohols which are adducts of approxi-
mately 2 to 15 molecules of ethylene oxide and/or propylene oxide with fatty alco-
hols having 8 to 22 carbon atoms.
Preferred anionic surfactants are alkyl sulfates and alkyl polyglycol ether sulfates
having 10 to 18 carbon atoms in the allcyl group and up to 12 glycol ether groups in the
; molecule.
Shampoos based on anionic surfactants are pre~erred hair treatment preparations
according to the invention.
Preferred cationic surfactants in the hair treatment preparations according to the ~ -
! invention are quaternary ammonium compounds, such as aL~cyl trimethyl ammonium chlor-
ides, diaLkyl dimethyl ammonium chloride and trialkyl methyl ammonium chlorides, for
;' 30 example cetyl trimethyl ammonium chloride, stearyl trimethyl amrnonium chloride, distear-
yl dimethyl ammonium chloride, lauryl dirnethyl ammonium chloride, lauryl dimethylbenz-
yl ammonium chloride and tricetyl methyl arnmonium chloride. Examples of other suit-
able cationic surfactants are cetyl pyridinium chloride, tallow alkyl tris-(oligooxyaL~yl)-am-
6 `:
':
~' ..
~ t
` ` 2~3{~3~
monium phosphate and the compounds disclosed in DE-A-34 42 175.
Hair rinses bascd on cationic surfactants are also preferr~d hair Ireatment prcpara-
tions according lo the invention.
Zwitterionic surfactants are surface-active compoonds which contain at least ones quaternary ammonium group and at least one -COO~~~ or -S03(-) group in Ihe molecule.
Particularly suitablc zwitterionic surfactants are the so-called betaines, such as N-aLkyl-
N,N-dimethyl ammonium glycinates, for example coconut oil alkyl dimethyl ammonium
glycinate, N-acyl aminopropyl-N,N-dimethyl arnmonium glycinates, for example coconut
oil acylaminopropyl dimethyl ammonium glycinate, and 2-aL~cyl-3-carboxymethyl-3-hy-
lO droxyethyl imidazolines having 8 to 18 carbon atoms in the aLkyl or acyl group and alsococonut oil acylaminoethyl hydroxyethylcarboxymethyl glycinate. A preferred zwitterionic
surfactant is the fatty acid amide derivative known by the Cl FA name of Cocamidopropyl
Betaine.
Ampholytic surfactants are surface-active compounds which, in addition to a C8 ,8
15 alkyl or acyl group, contain at least one free amino group and at least one -COOH or
-SO3H group in the molecule and which are capable of forming inner salts. Examples of
suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl.~in-
obutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl gly-
cines, N-alkyl taurines, N-alkyl sarcosines, ~-alkylaminopropionic acids and alkylamino-
20 acetic acids having approximately 8 to 18 carbon atoms in the alkyl group. Particularlypreferred ampholytic surfactants are N-coconut oil alkylaminopropionate, coconut oil acyl-
aminoethyl arninopropionate and Cl2 18 acyl sarcosine~
Nonionic surfactants contain, for exarnple, a polyol group, a polyalkylene glycol
ether group or a combination of polyol and polyglycol ether groups as their hydrophilic
25 group. Such compounds are, for example,
- adducts of 2 to 30 moles of ethylene oxide and/or O to 5 molecules of propylene
oxide with linear fatty alcohols having 8 to 22 carbon atoms, with fatty acids hav-
ing 12 to 22 carbon atoms and with alkylphenols having ~ to 15 c~bon atoms in
the alkyl group,
- C,2 22 fatty acid monoesters and diesters of adducts of 1 to 30 molecules of ethyl-
ene oxide with glycerol.
- glycerol monoesters and diesters and sorbitan monoesters and dies~ers of saturated
and unsaturated C8-22 fatty acids and ethylene oxide adducts thereof,
21 ;~~J ~3 ~i iJ ~
- C8 22 alkyl mono- and oligoglycosides and elhoxylated analogs thereof and
- adducts of 5 to 60 moles of e~hylene oxide with castor oil and hydrogenated castor
oil.
Particularly preferred nonionic surfactants are C~22 alkyl mono and oligoglyco-
s sides, of which the production and use as surfaclants are known, for example, from US
3,839,318, US 3,707,535, US 3,547,828, DE-A-19 43 689, DE-A-20 36 4~2 and DE-A-30
01 064 and from EP-A-77 167. They are prepared in particular by reaction of glucose or
oligosaccharides ~ ith primary alcohols having 8 to 22 carbon atoms. So far as the glyco-
side component is concerned, both monoglycosides in which a cyclic sugar unit is attached
~o to the fatty alcohol by a glycoside bond and oligomeric glycosides having a degrss of
oligomerization of up to preferably about 8 are suitable. Degrees of oligomerization of
1.4 and lower are particularly preferred. The degree of oligomerization is a statisdcal
mean value on which a homolog distribution typical of such products is based.
It has been found that the effect of the combination according to the invention is
further enhanced if the hair treatment preparation addidonally contains a nonionic surfact-
ant. This is particularly the case where the nonionic surfactant is a C8 2~ alkyl mono- and
-oligoglycoside.
Accordingly, preparations additionally having a nonionic surfactant, more particu-
larly a C8.22 alkyl mono-and -oligoglucoside, are preferred for the purposes of the inven-
tion.
The compounds having alkyl groups used as surfactants may bs individual sub-
stances. However, these substances are preferably produced from natural vegetable and
animal starting materials so that mixtures of substances differing in their alkyl chain
lengths according to the paIticular statting materials are obtained.
The surfactants formed by adducts of ethylene and/or propylene oxide with fatty
alcohols or derivatives of these adducts may be both normal-range products and also nar-
row-n~nge products. Normal-range products are understood to be mixtures of homologs
which are obtained in the reaction of fatty alcohol and aL~ylene oxide using alkali metals,
aL~cali metal hydroxides or aLkali metal alcoholates as catalysts. By contrast, narrow-range
products are obtained when, for example, hydrotalcites, ak~caline earth metal salts of ether
carboxylic acids. alkaline earth metal oxides, hydroxides or alcoholates are used as cata-
Iysts. It may be preferable to use narrow-range products. -The preparations according to the invention preferably contain surface-active com-
.
pounds in quantities of 0.1 to 50 % by weight, based on the preparation as a whole.
i Other typical consti~uents of hair keatrnent preparations are:
- cationic, anionic and llonionic polymers, such as for example quaterniæd cellulose
ethers, polysiloxanes, vinyl pyrrolidone copolymers, acrylamide/dimethyl diallyl`~ 5 ammonium chloride copolymers, vinyl acetate/ crotonic acid copolymers, polyvinyl
pyrrolidone and polyacrylic acids;
~¦ thickeners, such as for exarnple cellulose ethers, uncrosslinked and polyol-cross-
linked polyacrylic acids, agar-agar, guar gum, alginates and xanthan gums;
- protein hydrolyzates, more particularly elastin and collagen hydrolyzates;
10 - perfume oils
.1 solubiliærs, such as ethanol, isopropanol, ethylene glycol, propylene glycoL glyc-
¦ erol and diethylene glycol;
- dyes;
- substantive dyes for dyeing and tinting the hair;
15 _ oxidation dye precursors (primary intermediate and coupler components) for dye-
ing and tinting the hair;
- reducing agents, such as thioglycolic acid, for splitting the disulfide bridges in
permanent waving;
- oxidizing agents, such as potassium bromate and hydrogen peroxide, for fixing in
perrnanent waving;
. - antidandruff agents, such as piroctone olamine and ~inc omadine;
- pH regulators, such as citric acid/sodium citrate buffer;
- active substances, such as panthenol, allantoin, vegetable extracts and vitamins;
- light stabilizers;
25 - consistency regulators, such as sugar esters, polyol esters or polyol alkylethers;
- fats and waxes, such as spermaceti, beeswax, montan wax, paraffins and fatty al-
cohols; :
- superfatting agents, such as polyethoxylated lanolin denva~ives, lecithin derivatives
and fatty acid alkanolamides;
30 - complexing agents, such as EDTA and phosphonic acids; ` ~-
- swelling and penetration agents, such as glyceroL propylene glycol monoethyl eth-
er, guanidines and urea;
- opacifiers, such as latex;
.: :'
. g , . ~ ~
3 ~ ~
,
, - pearlescers, such as ethylene glycol mono- and -distearate;
propellents, such as propane/butane mixtures, N20, dimethyl ether and air; and
antioxidants.
The preparations according to the invention have a pH value preferably in ~he
s range from 3.5 to 10 and more preferably in the range from 4.5 to 9.
Hair treatment products in which the preparations according to the invention maybe used are, for example, shampoos, shower baths, rinses, hair dyes, hair tints, permanent
wave preparations, pennanent wave fixing prelparations, setting lotions, setting gels, hair
tonics, hair creams and hair lotions.
These hair treatment products may be fonnulated as typical hair treatrnent prepara-
tions, for example in the form of an aqueous solution or emulsion, an aqueous-alcoSIolic
or alcoholic solution, a crearn, a gel, a lotion or an aerosol.
The present invention also relates to the use of the prepa~ations clairned in any of
claims I to 11 for the treatment of hair and more particularly for the washing and care of
15 hair. This encompasses both treatrnents in which the hair is rinsed after the treatment and
treatments in which the preparation remains on the hair. The preparations according to
the invention have proved to be particularly advantageous in cases where the hair is rinsed
after a certain contact time of the treatment preparation.
Examples
Shampoos of the foilowing composidon (in % by weight) were used for the tests:
C Sl S2 S3 S4 SS S6 S7 S8 S9
Texapon(g)N 25~ 9.0 9.0 9 0 9.0 9 0 9.0 9.0 9.0 9.0 9.0 :
Akypo(~ RLM 100 NV2 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0
Dehyton(~K3 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0
2s Nutrilan(3 I4 0.5 05 05 0.5 05 0.5 0.5 0.5 05 05
Polymer Pl5 - 0.5 1.0 - - 0.5 0.5 0.5 1.0 1.0
Ajidew(~)N506 5 0 10.0 5.0 10.0 5.0 5.0 S.0
Alkyl glucoside - - - - - - - 2.0 - ~ 2.0
APG-6007
50 Water ad 100 100 100 100 100 100 100 100 100 100
Sodium lauryl ether sulfate; Cl FA name: Sodium Laureth Sulfate (approximately
28 % of acdve substance in water) (HENKEL)
~ ~
?1 ~ ~09
.
2 Cl2.~4-alkyl-O-(cH2cH2-O)~0-s:~H2-cooNa (22% of active subs~ance in water)
(CHEM-Y)
3 Fatty acid amide derivative of betaine structure with the formula R-CONH-(CH2)3-
N~(CH3)2-CH2-COO-; CTFA name. Cocamidopropyl Betaine (approximately 30 %
s of active substance in water) (HENKEL)
4 Protein hydrolyzate; CTFA narne: Hydrolyzed Animal Collagen (GRUNAU)
5 Polymer of acrylarnidopropyl trimethyl ammonium chlolide and acrylic acid
(molar ratio 3:1 ) oeutralized with sodium hydroxide according to DE-A-39 29 973.
Particulars of the preparation of the polymer can be found in thal document.
~o 6 Sodium salt of dl-2-pyrrolidone-5-carboxylic acid (50 % aqueous solution)
(AJINOMOTO).
7 Aqueous solution of RO(Z),~
with Z = glucose, x = 1.4 and R = n-alkyl (C12.14)~ (50 % of active substance)
(HORIZON)
'5 The moisture retention capacity, the curl retention capacity and the swelling of pig
epidermis, which is a measure of the skin compatibility of the preparation, were de-
termined.
1. Moisture retention capacity
The moislure relention capacity is a measure of the extent to which the hair retains
21! its natural water content in a dry environment.
The measurement was carried out on standardized mid-brown European hair (Al-
kinco 6634; tress weight: 2 g).
Pretreatment:
The hair tresses were first washed with an aqueous solution of Texapon N25 (1225 ~b of active substance) and dried in air.
Determination of the zero value: ~-
- The hair tresses were left for 24 hours at room temperature/95% relative air hu-
midity. The weight of the hair deterrnined thereafter was recorded as mH. The hair tress-
es were then dried over phosphorus pentoxide for 24 hours at room temperature. The
so quantity of water given off from the hair, which was determined from the increase in the
weight of the phosphorus pentoxide, was recorded as mw. Finally, the hair tresses were
redried for about 30 minutes at 50 C in a recirculating air drying cabinet to constant
;~ weight; the weight of the dry hair was recorded as m~,O.
! Measuremen~:
The same hair tresses were Ireated for 5 minutes with the shampoo and then rinsed
with water for 30 seconds. This operation was repeated five times. The variables m~, mw
l 5 and mHO were then dete~mined in the same way as the zero value.
15 Hair tresses were used for each measurement.
The results of the measuremen~s are set out in Table 1:
Water absorptio~ (mH-m~
Residual water content (mlrm~lo)-mw
o The values obtained in the zero measurement (water content at 95 % reladve air
i~ humidity: 18 % of the hair weight; water content after storage over phosphorus pentoxide:
3 % of the hair weight) were put at 100 %.
Table 1: Moisture retention capacity
ShampooWater absolption Residual water content
Zero value 100 % 100 %
C 100%100%
Sl 1~0%100%
S3 109%113% .
S4 108 % 127 %
SS 110%121 %
S6 112%135%
.. ..
2. Skin compatibilib t~sts
The skin compadbility of the shampoos was determined by the in vitro method
developed by Zeidler and Reese which is described in detail in the journal Arztliche
Kosmetologie lTitle in English: Medical Cosmetology] 13, 39~5 (1983).
The swelling of pig epidermis was used as a measure of the skin compadbility of
the shampoos. To this end, the epidermis required was taken from young pigs immedi-
30 ately after their slaughter and deep-cooled.
For the measurement, I cm x 6 cm strips stamped out from the epidermis were im-
mersed in the sharnpoos (diluted with water to a surfactant content of 2 % by weight~
which had been heated to 39 C and adjusted to pH 6.5. The weight of the swollen strips
12
?...~ 3
was then deterrnined after brief rinsing and removal of the adhering water by gentle
squeezing under defined conditions. The strips were then dried over calcium chloride for
24 hours and reweighed. To eliminate any influences attributable to ~he specific properties
of the particular animal or the point of removal (back, flank), a standard measurement was
5 carried out in each case. To this end, an immediately adjacent epidermis strip was simi-
larly treated with water instead of the shampoo.
The values s for the shampoo treatment and w for the treatment with water may
be calculated on the basis of the following rel~tion:
weight (swollen epidermis) - weight (dry epidermis)
S,W =
weight (dry epidermis)
Finally, the standardized relative change in swelling S is defined as:
S= [(s/w)-11 100%
By definition, therefore, the S value of the skin treated with water is 0 %; negative
,s values are indicative of swelling-inhibiting properties.
The results of the swelling measurements are set out in Table 2.
Table 2: Changes in swelling
Shampoo S value
C 50+7
Sl 46+6
S3 40 + 5 ..
S5 33+6
S7 24+7
_ _
3. Curl retention capacib
A 15 cm long hair tress (ALkinco 6634; tress weight: 2 g) was wound onto a glasstube with an external diameter of 1.7 cm, fixed and treated with 0.2 g of the shampoo.
The hair tresses were then rinsed with water and dried. A measure of the stability of the
curl obtained after withdrawal of the glass rod is the curl retention value. The curl reten-
tion value is defined as ~ /(l-lo)] 100 %, where I is the length of the hair tress (15
cm~, lo is the ]ength of the hair tress immediately drying and 1~ is the length of the hair
tress after storage in a drying cabinet for 48 h under constant conditions (30 C/40 % rela-
''"-S
tive air humidity). The resul~s of ~he measurements are se~ out in Table 3.
J - - - -` --. ~. ~
~ Table 3: Cu.l rctention values
~1'
s Sharnpoo Curl retention value
1 C 87.1
:~, S2 94.7
S3 85
S8 96.2
o S9 96.8
4. Application Examples
4.1. Hair rinse
Components % by weight -
15 Texapon~N 25 5.0
Dehyton(5~)K 1.0
Polymer pl8 2.5
Ajidew~N50 2.0
Water ad 100
:~
. 8 20 % of active substance in water ~ -
. 4.2. Hair rinse
Cornponents % by weight
Texapon~N 25 5 0
Dehyton(9AB 309 l 0
Polyiner pl8 3.0
: Ajidew(~N50 3.0
Water ad 100
~o 9 Fatty amine derivative of betaine structure; CTFA name: Coco-Betaine (approxi-
mately 30 % of active substance in water) (HENKEL)
;
. :
14 ~:
.. ; .
3 ~
4.3. Hair ~inse
Components % by weight
Texapon~sB 3' 0 9
Texapon(~K14 S spez." 1.2
s Dehyton~AB 30 1.0
Polymer pl8 1.5
Ajidew~N50 2.0
Water ad 100
0 Sulfosuccinic acid semiester based on a C12 ~4 alkyl poly(3-EO) glycol ether, disod-
ium salt; CTFA narne: Disodium Laureth Sulfosuccinate (40 % of active substance
in water) (HENKEL)
" Sodium lauryl myristyl ether sulfate (approximately 30 % of active substance in
water) (HENKEL)
4.4. Hair rinse
Components % by weight
Texapon~SB 3 1.0
Dehyton(~AB 30 7.5
Polymer pl8 2.5
Ajidew(~NS0 2.0
Water ad 100
4.5. Hair rinse
Components % by weight
C,6 ,8 fatty alcohol 3.0
Dehyton(5 )K 8.0
Texapont~N 25 5.0
Polymer pl8 2.5
Ajidew(~NS0 5.0
Water ad 100
To prepare this hair rinse, the rnixture of surfactants and polymer was introduced .:
into the molten fatty phase and emulsified therein.
3 ~ 13~
4.6. Hair shampoo
Components S~ by weight
Texapon(3N 25 50.0
Dehyton(~K 1 0.0
Pol~/mer pl8 5,0
Ajidew(~N50 10~0
Water ad 100
4.7. Hair shampoo
Components % by weight
Texapon(~N 25 45.û
Dehyton(3 K 15.0
Akypo(~RLM 100 NV 5.0
Polymer pl8 5 0
Ajidew(~)A 10012 2.0
Water ad 100
12 dl-2-pyrrolidone-5-carboxylic acid (AJINOMOTO)
4.8. Hair shampoo
Components % by weight
Texapon(~K14 S spez. 15~0
Texapon(~)SB 3 12~0
Ethoxylated (9 EO) palm kernel
oil fatty acid 1.0
AL~cyl glucoside APG-600 4.0
Dehyton6)CB'3 9.7
Polymer pl8 3 0
Ajidew(~)N50 2.0
Water ad 100
~o '3 Aqueous solution of a fatty amine derivative of betaine structure; CTFA name:
Coco-Betaine (app;oximately 31 % of active substance, approximately 6.5 % of
NaCl) (HENKEL)
,.
16
4.9. Hair shampoo
-, Components % by weight
TPxapon(~SB 3 12.0
~, Ethoxylated (9 EO) palm kernel
oil fatty acid 1.0
¦ Dehyton(~CB 10.0
~¦ Eucarol~ TA'4 20.0
Polymer p l 8 1.2
Ajidew(~)N50 3.0
10 Water ad 100
14 Aqueous solution of sodium laureth-7-tartrate (25 % of active substance) (ROL)
2.1û. Hair shampoo
Components % by weight
15 Texapon(~SB 3 15.0
Dehyton~CB 12.0
Alkyl glucoside APG-600 4.0
Polymer pl8 1.2
Ajidewq~N50 3.0
20 Water ad 100
