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Patent 2139495 Summary

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(12) Patent Application: (11) CA 2139495
(54) English Title: HAIR TREATMENT PREPARATION
(54) French Title: PREPARATION POUR LE TRAITEMENT DES CHEVEUX
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • A61K 08/73 (2006.01)
  • A61K 08/49 (2006.01)
  • A61K 08/81 (2006.01)
  • A61K 08/891 (2006.01)
  • A61Q 05/00 (2006.01)
  • A61Q 05/02 (2006.01)
  • A61Q 05/04 (2006.01)
  • A61Q 05/10 (2006.01)
(72) Inventors :
  • SEIDEL, KURT (Germany)
  • MUELLER, REINHARD (Germany)
  • HOLLENBERG, DETLEF (Germany)
  • PRIEBE, CHRISTIAN (Germany)
(73) Owners :
  • HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN
(71) Applicants :
  • HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN (Germany)
(74) Agent: SWABEY OGILVY RENAULT
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1993-06-24
(87) Open to Public Inspection: 1994-01-20
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP1993/001625
(87) International Publication Number: EP1993001625
(85) National Entry: 1995-01-03

(30) Application Priority Data:
Application No. Country/Territory Date
P 42 21 914.0 (Germany) 1992-07-03
P 42 32 512.9 (Germany) 1992-09-29
P 42 34 405.0 (Germany) 1992-10-13
P 42 34 413.1 (Germany) 1992-10-13

Abstracts

English Abstract


The use of water-based hair treatment preparations containing a
combination of cellulose-based cationic polymers with zwitterionic polymers
produces a very significant improvement in wet combability and a shift in dry
combability into an optimal range for style retention.


Claims

Note: Claims are shown in the official language in which they were submitted.


New Claim 1
1. A water-based preparation for the treatment of hair
containing a combination of cationic and zwitterionic
polymers in addition to typical cosmetic components,
characterized in that the cationic polymers are cellulose
derivatives and do not contain any imidazolinium groups and
the zwitterionic polymers are essentially composed of
.alpha.) monomers containing quaternary ammonium groups corre-
sponding to general formula (I):
R1-CH=CRZ-CO-Z-(CnH2n)-N(+)R3R4R5 A(-) (I)
in which R1 and R2 independently of one another
represent hydrogen or a methyl group and R3, R4 and R5
independently of one another represent alkyl groups
containing 1 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
anion of an organic or inorganic acid
and
.beta.) monomeric carboxylic acids corresponding to general
formula (II):
R6 CH=CR7-COOH (II)
in which R6 and R7 independently of one another
represent hydrogen or methyl groups,
or alkali metal, alkaline earth metal, aluminium or
ammonium salts of these acids.

27
CLAIMS
2. A preparation as claimed in claim 1, charac-
terized in that the cationic polymer is a copolymer of
at least one cationic unit and at least one nonionic
unit.
3. A preparation as claimed in claim 2, charac-
terized in that the nonionic unit is hydroxyethyl
cellulose.
4. A preparation as claimed in any of claims 1 to 3,
characterized in that the zwitterionic polymers consist
essentially of
(.alpha.) monomers containing quaternary ammoniun groups
corresponding to general formula (I):
R1-CH=CR2-CO-x-(CnH2n)-N(?)R3R4R5 A(-) (I)
in which R1 and R2 independently of one another
represent hydrogen or a methyl group and R3, R4
and R5 independently of onc another represent C1-4
alkyl groups, X is an NH group or an oxygen atom,
n is an integer of 2 to 5 and A(-) is the anion of
an organic or inorganic acid
and
(.beta.) mononeric carboxylic acids corresponding to
general formula (II):
R6-CH=CR1-COOH (II)
in which R6 and R7 independently of one another

28
are hydrogen or methyl groups,
or alkali metal, alkaline earth metal, aluminium
or ammonium salts of these acids.
5. A preparation as claimed in claim 4, charac-
terized in that the monomer (.alpha.) is acrylamidopropyl
trimethyl ammonium chloride while while the monomer (.beta.)
is acrylic acid or an alkali metal salt, particularly
the sodium salt, of acrylic acid.
6. A preparation as claimed in claim 4 or 5,
characterized in that the number of monomers (.alpha.) in the
zwitterionic polymer is greater than the number of
monomers (.beta.).
7. A preparation as cliamed in any of claims 1 to 6,
characterized in that it contains
- 0.01 to 10% by weight ans more particularly 0.01
to 5% by weight zwitterionic polymers and
- 0.01 to 10% by weight and more particulary 0.01
to 5% by weight cationic polymers,
based on the preparation as a whole.
8. A preparation as claimed in any of claims 1 to 7,
characterized in that it also contains a surfactant.
9. A preparation as claimed in claim 8, character-
ized in that the surfactant is a cationic and/or non-
ionic surfactant.
10. A preparation as claimed in any of claims 1 to
9, characterized in that the preparation has a pH value
of 2.5 to 7 and, more particularly, in the range from
3.0 to 6Ø
11. A process for treating hair, characterized in
that a preparation as claimed in any of claims 1 to 10
is applied to the hair.
12. A process as claimed in claim 11, characterized
in that the hair is subsequently rinsed with water or
with a preparation largely containing water.

Description

Note: Descriptions are shown in the official language in which they were submitted.


- - ~139~9~
H 470 PCT / 28.05.1993
~air treatment preparations
This invention relates to hair treatment prepara-
tions containing a special combination of polymers.
The washing and care of hair is an important part
of personal hygiene. Both the washing of hair with
shampoos and the decorative finishing of hair styles,
for example by coloring or permanent waving, are meas-
ures which affect the natural structure and properties
of hair. For example, the wet and dry combability of
hair, its hold and its body can be adversely affected
or the number of split ends can be increased by such
measures.
Accordingly, it has long been standard practice
to subject the hair to a special aftertreatment. To
this end, the hair is treated, normally by rinsing, with
special active substances, for example quaternary
ammonium salts or special polymers. ComhAhility, hold
and body are improved and the number of split ends are
reduced by this treatment, depending on the formulation
of the preparation used.
Additions of cationic polymers to hair treatment
preparations generally lead to an improvement in wet and
dry combability. Additions of amphoteric or zwitterion-
ic polymers produce significant improvements in wet
romh~hility but generally have little effect on dry
combability.
Other positive effects can often be obtained by
combining several active substances from different
classes. Thus, it is known from DE-A1-30 44 738, for
example, that hair treatment preparations can be pro-
vided with a mixture of amphoteric and cationic poly-
mers.
Whereas the improvement in wet combability, i.e.

2139~9~
H 470 PCT 2
a reduction in wet combing work, is desirable in every
case, the circumstances regarding dry combability are
more complicated. Low combing work values characterize
an improvement in ro~h~hility. However, if combing work
is overly reduced, the hair loses body and hold so that,
in extreme cases, certain styles can no longer be
created. Accordingly, a certain increase in dry combing
work may be entirely desirable, above all in the case
of relatively intricate styles, in order to improve
style retention.
It has now surprisingly been found that prepara-
tions cont~ining a combination of zwitterionic polymers
and certain cationic polymers produce a surprisingly
good improvement in the properties of hair.
Accordingly, the present invention relates to
water-based hair treatment preparations cont~;ning a
combination of cationic and zwitterionic polymers in
addition to typical cosmetic constituents, characterized
in that the cationic polymers are cellulose derivatives
and do not contain any imidazolinium groups.
The cationic polymers suitable for use in accord-
ance with the invention are cellulose derivatives.
One class of these cellulose derivatives are the
substances obtained by modification of a cellulose base
with cationic groups.
Examples of cellulose bases are cellulose, methyl
cellulose, ethyl cellulose, hydroxyethyl cellulose,
hydroxypropyl cellulose and methyl hydroxypropyl cellu-
lose.
Typical cationic groups are groups containing
quaternary nitrogen or phosphorus atoms. Groups con-
taining quaternary nitrogen atoms are preferred. The
quaternary nitrogen atoms may contain four different
constituents or partly the same substituents and may
also be part of a ring system. Preferred substituents

2139~9~
H 470 PCT 3
are alkyl groups containing 1 to 4 carbon atoms, aryl
groups, alkylaryl groups, cycloalkyl groups, alkoxyalkyl
groups and alkoxyaryl ~LUU~s. Trialkyl ammonium groups,
particularly trimethyl ammonium groups, are particularly
preferred. The cationic groups may be attached to the
cellulose base either directly or by intermediate
groups. Preferred polymers are those in which the
cationic groups are attached to the cellulose base by
alkyl chains or alkoxyalkyl groups. Preferred counter-
ions to the cationic groups are halide groups, par-
ticularly chloride groups, and methosulfate groups.
Examples of such compounds are the compounds
described in US-PS 3,472,840 which are commercially
available under the name of Polymer J~.
Another class of cationic cellulose derivatives
are compounds made up of cationic and nonionic units.
The cationic units may be synthesized similarly
to the cationic cellulose derivatives mentioned above.
The cationic units may also be compounds which
contain at least one polymerizable group in addition to
at least one cationic group. The polymerizable group is
preferably a vinyl group. The cationic ~lOU~S are pref-
erably the ammonium groups mentioned above. Cationic
units such as these are, for example, diallyl dimethyl
ammonium chloride, methacrylamidopropyl trimethyl
ammonium chloride, dimethyl aminomethacrylate quater-
nized with diethyl sulfate and dimethyl aminoethyl
methacrylate quaternized with diethyl sulfate.
Nonionic units are, for example, cellulose,
methyl cellulose, ethyl cellulose, hydroxyethyl cel-
lulose, hydroxypropyl cellulose, methyl hydroxypropyl
cellulose, vinyl pyrrolidone, vinyl acetate, acrylamide,
methacrylamide, methyl acrylate, ethyl acrylate, methyl
methacrylate and ethyl methacrylate. Hydroxyethyl
cellulose is a preferred nonionic unit.

2139~9S
H 470 PCT 4
Examples of such copolymers are the compounds
obtainable under the name of Celquat.
Cationic polymers, which are copolymers of at
least ane cationic unit and at least one nonionic unit,
are preferred for the purposes of the present invention.
Copolymers in which the nonionic unit is hydroxyethyl
cellulose are particularly preferred.
Celquat~L 200, a copolymer of hydroxyethyl
cellulose and diallyl dimethyl ammonium chloride, is a
particularly preferred cationic polymer.
"Zwitterionic polymers" are polymers which
contain quaternary ammonium groups and -COO~ or -S03-
groups in the molecule.
Examples of zwitterionic polymers suitable for
use in accordance with the invention are the compounds
mentioned in GB-A-2,104,091, in EP-A 47 714, in EP-A-283
817 and in DE-A-28 17 369.
Zwitterionic polymers consisting essentially of
the following monomers are particularly preferred:
(~) monomers containing quaternary ammonium groups
corresponding to general formula (I):
Rl-CH=CR2-Co-x-(cnH2n)-N(+)R3R4R5 A(-) (I)
in which Rl and R2 independently of one another
represent hydrogen or a methyl group and R3, R4
and R5 independently of one another represent C~
alkyl groups, X is an NH group or an oxygen atom,
n is an integer of 2 to 5 and A( ~ is the anion of
an organic or inorganic acid
and
(B) monomeric carboxylic acids corresponding to
general formula (II):

2139~9S
H 470 PCT 5
R6-C~=CR7-CooH (II)
in which R6 and R7 independently of one another
are hydrogen or methyl groups.
According to the invention, these compounds may
be used both directly and also in salt form, i.e. after
neutralization of the polymers, for example with an
alkali metal hydroxide. Particulars of the production
of these polymers can be found in DE-A-39 29 973.
Polymers based on monomers (~), in which R3, R4
and R5 are methyl groups, X is an NH group and A~) is a
halide, methoxysulfate or ethoxysulfate ion, are most
particularly preferred. Acrylamidopropyl trimethyl
ammonium chloride is a particularly preferred monomer
(~). Acrylic acid or an alkali metal salt of acrylic
acid, more particularly the sodium salt, is preferably
used as the monomer (~) for the polymers mentioned
above.
Other preferred zwitterionic polymers are those
in which the number of monomers (~) is greater than the
number of monomers (B). Ratios of the (~) to (B)
monomers of greater than 1.5 are particularly preferred.
Both cationic and zwitterionic polymers are
preferably present in the preparations according to the
invention in quantities of 0.01 to 10% by weight, based
on the preparation as a whole. Quantities of 0.01 to 5%
by weight are particularly preferred.
Preparations containing the cationic polymers and
zwitterionic polymers in quantity ratios of S:l to 1:1
have proved to be particularly effective.
It has also been found that particularly good
results are obtained in accordance with the invention if
the preparations according to the invention also contain
a surfactant. The surfactant may be an anionic, cation-

~139495
H 470 PCT 6
ic, ampholytic, zwitterionic or nonionic surfactant.
Examples of cationic surfactants suitable for use
in the hair treatment preparations according to the
invention are, in particular, quaternary ammonium
compounds, preferably ammonium halides, especially
chloride and bromides, such as alkyl trimethyl ammonium
chlorides, dialkyl dimethyl amm~nium chlorides and
trialkyl methyl ammonium chlorides, for example cetyl
trimethyl ammonium chloride, stearyl trimethyl ammonium
chloride, distearyl dimethyl ammonium chloride, lauryl
dimethyl ammonium chloride, lauryl dimethyl benzyl
ammonium chloride and tricetyl methyl ammonium chloride.
Other cationic surfactants suitable for use in accord-
ance with the invention are quaternized protein hydroly-
zates.
Also suitable for the purposes of the invention
are silicone oils, such as for example the commercially
available products Q2-7224 (a stabilized trimethyl silyl
amodimethicone; a product of Dow Corning), Dow Corning
929 Emulsion (containing a hydroxylamino-modified
silicone which is also known as amodimethicone), SM-2059
(General Electric), SLM-55067 (Wacker) and ABIL~-Quat
3270 and 3272 (Th. Goldschmidt; diquaternary polydimeth-
yl siloxanes, Quaternium-80).
Apart from a favourable conditioning effect,
alkyl amidoamines, particularly fatty acid amidoamines,
such as the stearyl amidopropyl dimethyl amine commer-
cially available as TEGO AMIDE~ S 18, are distinguished
in particular by their ready biodegradability.
So-called esterquats, such as the dialkyl ammoni-
um methosulfates and methyl hydroxyalkyl dialkoyloxy-
alkyl ammonium methosulfates marketed under the name
STEPANTEX~, are also readily biodegradable.
One example of a quaternary sugar derivative
suitable for use as a cationic surfactant is the commer

- 2139~9S
H 470 PCT 7
cial product GLUCQUAT~ of which the CTFA name is Lauryl
Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride.
Particularly preferred cationic surfactants are
alkylamidoamines, quaternary ester compounds and quater-
nary sugar derivatives.
Anionic surfactants suitable for the preparationsaccording to the invention are any of the anionic sur-
factants which are suitable for use on the human body.
They are characterized by a water-solubilizing anionic
group, for example a carboxylate, sulfate, sulfonate or
phosphate group, and a lipophilic alkyl group containing
approximately 10 to 22 carbon atoms. Glycol or polygly-
col ether groups, ester, ether and amide groups and also
hydroxyl groups may also be present in the molecule.
The following are examples of suitable anionic surfac-
tants in the form of the sodium, potassium and ammonium
salts and also the mono-, di- and trialkanolammonium
salts containing 2 or 3 carbon atoms in the alkanol
group:
- linear fatty acids containing 10 to 22 carbon
atoms (soaps),
- ether carboxylic acids corresponding to the
formula R-0-(CH2-CH20)~-CH2-COOH, in which R is a
linear alkyl group containing 10 to 22 carbon
atoms and x = 0 or 1 to 16,
- acyl sarcosides containing 10 to 18 carbon atoms
in the acyl group,
- acyl taurides containing 10 to 18 carbon atoms in
the acyl group,
- acyl isethionates containing 10 to 18 carbon
atoms in the acyl group,
- sulfosuccinic acid mono- and dialkyl esters con-
taining 8 to 18 carbon atoms in the alkyl group
and sulfosuccinic acid monoalkyl polyoxyethyl

213949~
H 470 PCT 8
esters containing 8 to 18 carbon atoms in the
alkyl group and 1 to 6 oxyethyl groups,
- linear alkane sulfonates containing 12 to 18
carbon atoms,
- linear alpha-olefin sulfonates containing 12 to
18 carbon atoms,
- alpha-sulfofatty acid methyl esters of fatty
acids containing 12 to 18 carbon atoms,
- alkyl sulfates and alkyl polyglycol ether sul-
fates corresponding to the formula R-O(CH2-CH20)~-
OSO3H, in which R is a preferably linear alkyl
group containing 10 to 18 carbon atoms and x = O
or 1 to 12,
- mixtures of surface-active hydroxysulfonates
according to DE-A-37 25 030,
- sulfated hydroxyalkyl polyethylene and/or hy-
droxyalkyl propylene glycol ethers according to
DE-A-37 23 354,
- sulfonates of unsaturated fatty acids containing
12 to 24 carbon atoms and 1 to 6 double bonds
according to DE-A-39 26 344,
- esters of tartaric acid and citric acid with
alcohols which are adducts of approximately 2 to
15 molecules of ethylene oxide and/or propylene
oxide with fatty alcohols containing 8 to 22
carbon atoms.
Preferred anionic surfactants are alkyl sulfates,
alkyl polyglycol ether sulfates and ether carboxylic
acids containing 10 to 18 carbon atoms in the alkyl
group and up to 12 glycol ether groups in the molecule
and also sulfosuccinic acid mono- and dialkyl esters
containing 8 to 18 carbon atoms in the alkyl group and
sulfosuccinic acid monoalkyl polyoxyethyl esters con-
taining 8 to 18 carbon atoms in the alkyl group and 1 to
6 oxyethyl groups.

213949S
H 470 PCT 9
Zwitterionic surfactants are surface-active
compounds which contain at least one quaternary ammonium
group and at least one -COO~ or -SO3() group in the
molecule. Particularly suitable zwitterionic surfac-
tants are the so-called betaines, such as the N-alkyl-
N,N-dimethyl ammonium glycinates, for example cocoalkyl
dimethyl ammonium glycinate, N-acylaminopropyl-N,N-
dimethyl ammonium glycinates, for example cocoacyl
aminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-
carboxymethyl-3-hydroxyethyl imidazolines containing 8
to 18 carbon atoms in the alkyl or acyl group and coco-
acyl aminoethyl hydroxyethyl carboxymethyl glycinate.
A preferred zwitterionic surfactant is the fatty acid
amide derivative known by the CTFA name of Cocamidopro-
pyl Betaine.
Ampholytic surfactants are surface-active com-
pounds which, in addition to a CB_18 alkyl or acyl group
in the molecule, contain at least one free amino group
and at least one -COOH or -SO3H group and which are
capable of forming inner salts. Examples of suitable
ampholytic surfactants are N-alkyl glycines, N-alkyl
propionic acids, N-alkyl aminobutyric acids, N-alkyl
iminodipropionic acids, N-hydroxyethyl-N-alkyl amidopro-
pyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-
alkyl aminopropionic acids and alkyl aminoacetic acids
all containing approximately 8 to 18 carbon atoms in the
alkyl group. Particularly preferred ampholytic surfac-
tants are N-cocoalkyl aminopropionate, cocoacyl amino-
ethyl aminopropionate and C12-1B acyl sarcosine.
Nonionic surfactants contain, for example, a
polyol group, a polyalkylene glycol ether group or a
combination of polyol and polyglycol ether groups as the
hydrophilic group. Examples of compounds such as these
are

2139495
H 470 PCT 10
- adducts of 2 to 30 mol ethylene oxide and/or 0 to
5 mol propylene oxide with linear fatty alcohols
containing 8 to 22 carbon atoms, with fatty acids
containing 12 to 22 carbon atoms and with alkyl-
phenols containing 8 to 15 carbon atoms in the
alkyl group,
- Clz22 fatty acid monoesters and diesters of
adducts of 1 to 30 mol ethylene oxide with
glycerol,
- C~22 alkyl mono- and oligoglycosides and ethoxy-
lated analogs thereof and
- adducts of 5 to 60 mol ethylene oxide with castor
oil and hydrogenated castor oil.
The compounds containing alkyl groups used as
surfactants may be individual substances. However, it
is generally preferred to produce the compounds in
question from native vegetable or animal raw materials
so that mixtures of compounds differing in their chain
length according to the particular raw material used are
obtained.
The surfactants which are adducts of ethylene
and/or propylene oxide with fatty alcohols or deriva-
tives of such adducts may be both products having a
"normal-range" homolog distribution and also products
having a "narrow-range" homolog distribution. "Normal-
range" products are mixtures of homologs which are
obtained in the reaction of fatty alcohol and alkylene
oxide using alkali metals, alkali metal hydroxides or
alkali metal alcoholates as catalysts. By contrast,
narrow-range products are obtained when, for example,
hydrotalcites, alkaline earth metal salts of ether
carboxylic acids, alkaline earth metal oxides, hydroxr
ides or alcoholates are used as catalysts. It may bebe
preferable to use narrow-range products.

2139~95
H 470 PCT 11
The quantity of surfactants which may be present
in the preparations according to the invention is
dependent upon the particular type of surfactant and the
purpose for which the preparation is intended.
Hair aftertreatment preparations preferably con-
tain cationic and/or nonionic surfactants, more particu-
larly in quantities of 0.1 to 10% by weight, based on
the preparation as a whole. Quantities of 0.1 to 3% by
weight are particularly preferred.
Hair tonics also preferably contain cationic
and/or nonionic surfactants, more particularly in quan-
tities of 0.1 to 10~ by weight, based on the preparation
as a whole. Quantities of 0.1 to 5% by weight are
particularly preferred.
Shampoos preferably contain anionic surfactants,
if desired in combination with ampholytic and/or non-
ionic surfactants, more particularly in quantities of 1
to 50% by weight, based on the preparation as a whole.
Quantities of 3 to 20% by weight are particularly
preferred.
The preparations according to the invention pref-
erably have pH values of 2.5 to 7 and, more particular-
ly, in the range from 3 to 6.
Shampoos, hair aftertreatment preparations and
hair tonics are preferred preparations according to the
invention. Neverthelessj the preparations may also be
permanent wave preparations, dyes, blow-wave prepara-
tions and other typical hair treatment preparations.
The preparations may be formulated as aqueous or
aqueous/alcoholic solutions, creams, lotions, gels,
emulsions and other typical cosmetic preparations.
The preparations may contain any other known
constituents according to the type of hair treatment
preparation and the particular formulation.
The constituents in question are:

213949~
H 470 PCT 12
- nonionic polymers such as, for example, vinyl
pyrrolidone/vinyl acrylate copolymers, polyvinyl
pyrrolidone and vinyl pyrrolidone/vinyl acetate
copolymers and polysiloxanes,
- anionic polymers such as, for example, polyacry-
lic acids, crosslinked polyacrylic acids, vinyl
acetate/crotonic acid copolymers, vinyl pyrroli-
done/vinyl acrylate copolymers, vinyl acetate/
butyl maleate/isobornyl acrylate copolymers,
methyl vinyl ether/maleic anhydride copolymers,
acrylic acid/ethyl acrylate/N-tert.butyl acryl-
amide terpolymers,
- other cationic polymers such as, for example,
quaternized cellulose ethers, polysiloxanes
containing quaternary groups, acrylamide/dimethyl
diallyl ammonium chloride copolymers and dimethyl
aminomethacrylate/vinyl pyrrolidone copolymers
quaternized with diethyl sulfate,
- thickeners, such as agar agar, guar gum, algin-
ates and xantham gum,
- structurants, such as glucose and maleic acid,
- hair-conditioning compounds, such as phospho-
lipids, for example soya lecithin, egg lecithin,
cephalins, and also silicone oils,
- protein hydrolyzates, more particularly elastin,
collagen, keratin, milk protein, soya protein and
wheat protein hydrolyzates, condensation products
thereof with fatty acids and quaternized protein
hydrolyzates,
- perfume oils, dimethyl isosorbide and cyclodex-
trins,
- solubilizers, such as ethanol, isopropanol,
ethylene glycol, propylene glycol, glycerol and
diethylene glycol,

~139995
~ .
H 470 PCT 13
- dyes,
- antidandruff agents, such as Piroctone Olamine
and Zinc Omadine-,
- other substances for pH adjustment,
- active substances, such as panthenol, allantoin,
pyrrolidone carboxylic acids, plant extracts and
vitamins,
- light stabilizers,
- consistency regulators, such as sugar esters,
polyol esters or polyol alkyl ethers,
- fats and waxes, such as spermaceti, beeswax,
montan wax, paraffins and fatty alcohols,
- fatty acid alkanolamides,
- complexing agents, such as EDTA, NTA and phos-
phonic acids,
- swelling and penetration agents, such as glycer-
ol, propylene glycol monoethyl ether, carbonates,
hydrogen carbonates, guanidines, ureas and
primary, secondary and tertiary phosphates,
- opacifiers, such as latex,
- pearlescers, such as ethylene glycol monostearate
and distearate,
- propellents, such as propane/butane mixtures, N2O,
dimethyl ether, CO2 and air and
- antioxidants,
- substantive dyes,
- so-called coupler and developer components as
oxidation dye precursors,
- reducing agents such as, for example, thioglycol-
ic acid and derivatives thereof, thiolactic acid,
cysteamine, thiomalic acid and ~-mercaptoethane-
sulfonic acid,
- oxidizing agents, such as hydrogen peroxide,
potassium bromate and sodium bromate.
The present invention also relates to a process

,2139g95
H 470 PCT 14
for treating hair using a preparation according to the
invention.
In a preferred embodiment of the process accord-
ing to the invention, preparations containing the
combination of active ingredients according to the
invention are applied to the hair and, after a certain
contact time, generally between a few seconds and about
20 minutes, are rinsed off from the hair either with
water or with a preparation largely containing water.
The following Examples are intended to illustrate
the invention.
E x a m p l e s
I. Determination of wet combability
Test methods
Wet combability was determined by two different
methods. Method 1 is based on the objective determina-
tion of wet combing work while method 2 is based on the
subjective assessment of examiners.
Method 1:
The combability tests were carried out by the
method according to J. 8OC. Cosm. Chem. 1973 ~24) 782.
Combing work was studied on brown hair (Alkinco
#6634, tress length 12 cm, tress weight 1 g). The hair
used was lightly predamaged (cold-waved or bleached)
hair which the average consumer would be expected to
have. After the zero measurement, the tresses were
soaked with 100 ml of the formulation to be tested.
After a contact time of 5 minutes, the tresses were
rinsed out for 1 minute in running water (1 l/min.,
38C). To determine wet combing work, the tresses were
then remeasured.

2139495
~.
H 470 PCT 15
Method 2:
Hair tresses weighing approximately 2 g (obtained
from the Kerling company) were predamaged by permanent
wave treatment and by "medium bleaching" (treatment of
the hair for 30 minutes with a 6% H2O2 solution adjusted
with ammonia to a pH value of 9.4). The tresses were
then washed twice with an aqueous solution of TEXAPON~
N 25 (sodium lauryl ether sulfate) adjusted to an active
substance content of 12%. The tresses were then treated
for 2 minutes with 0.5 g of the solution to be tested.
Finally, they were rinsed with water at 30C.
Results
The composition of the test mixtures and the
results of the combability tests are set out in Table 1.
The combing work values determined by method 1 are all
based on the value of the zero measurement. The scores
for the subjective assessment by method 2 ranged from 1
= very good through 2 = good, 3 = satisfactory and 4 =
adequate to 5 = unsatisfactory.
Table 1 (quantitie~ in part~ by weight)
Component / mixture C1 C2 I1 C3 C4
CELQUAT~L 200~ 0.1 - 0.05 - 0.05
Acrylamidopropyl methyl
ammonium chloride/acrylic
acid copolymer, neutralized
with sodium hydroxide
(Polymer Pl acc. to
DE 39 29 973) - 0.1 0.05 - -
AMPHOMER~ ~' - - - 0.1 0.05
Water <------- and 100 ------->
Wet combing work
- Method 1 [%] 64 46 43 85 72
- Method 2 2-3 2-3 1-2 3-4 3

2139495
H 470 PCT 16
Hydroxyethyl cellulose/diallyl dimethyl ammonium
chloride (95~ active substance; CTFA name: Poly-
quaternium-4) (DELFT NATIONAL)
~' Methyl methacrylate/tert.butyl aminoethyl meth-
S acrylate/2-hydroxypropyl methacrylate/N-(1,1,3,3-
tetramethylbutyl)-acrylamide copolymer
II. Determination of curl retention
Method
A 15 cm long tress (Kerling; tress weight 2 g)
was treated for 2 minutes with 0. 5 g of the mixture to
be tested. The tress was then rinsed and wound around
a glass tube with an external diameter of 2.0 cm, fixed
and dried. A measure of the stability of the curl
obtained after withdrawal of the glass tube is the so-
called curl retention value (CR value) which is defined
as ((l-1~)/(1-lo)) * 100%, where 1 is the length of the
hair tress (lS cm), lo is the length of the curl immedi-
ately after drying and 1~ is the length of the curl after
hanging for x hours in a drying cabinet under constant
conditions (25C/60% relative air humidity).
Results:
The results of the curl retention tests are set
out in Table 2.
Table 2
Measured value / mixture Cl C2 Il C3 C4
CR values after
- 6 hours [%] 81.4 82.6 86.5 88.4 82.9
- 8 hours [%] 79.8 80.7 83.7 86.2 81.3
The values for the treatment with pure water were

213~49~
. .
H 470 PCT 17
83.2 (after 6 hours) and 79.9 (after 8 hours).
III. Applic~tion Examples
S The quantities in the following Examples are %
by weight.
1) Hair rinse
STENOL016l82 3.0
CUTINA~9GMS2 0 . 5
EUMULGIN~B 14 O. 4
EUMULGIN~B 25 0.8
EUTANoL~G5 1.0
Acylamidopropyl methyl
ammonium chloride/acrylic
acid copolymer, neutral-
ized with sodium hydroxide
(polymer P1 acc. to
DE 39 29 973) 0.2
CELQUAT~L200 1.0
GAFQUAT~755-N5 2.5
Water ad 100
2 Cl6/ Cl8 fatty alcohol (HENKEL)
3 Glycerol monostearate (CTFA name: Glyceryl
Stearate) (HENKEL)
4 Cetostearyl alcohol containing approx. 12 mol EO
(CTFA name: Ceteareth-12) (HENKEL)
Cetostearyl alcohol containing approx. 20 mol EO
(CTFA name: Ceteareth-20) (HENKEL)
6 Condensation product of saturated liquid fatty
alcohols, primarily decyl alcohol, prepared by the
Guerbet reaction (CTFA name: Octyldodecanol)
(HENKEL)
7 Vinyl pyrrolidone/dimethylaminoethyl methacrylate
copolymer quaternized with diethyl sulfate (19%
active substance in water) (GAF)

2139~9~
H 470 PCT 18
2) Hair rinse
STANOL01618 1.8
TEGOAMID~S 18~ 1.6
1,2-Propylene glycol 1.0
Citric acid 0.6
CELQUAT0L 200 1.0
Polymer P1 acc. to DE 39 29 973 0.2
Perfume oil, water ad 100
o 8 N,N-dimethyl-N'-stearoyl-1,3-diaminopropane (CTFA
name: Stearamidopropyl Dimethylamine (GOLDSCHMIDT)
3) Hair rinse
STENOL~1618 1.8
STEPANTEX~VS 909 1.8
1,2-Propylene glycol 0.7
Citric acid 0.2
CELQUAT~L 200 1.2
Polymer Pl acc. to DE 39 29 973 0.3
Perfume oil, dye, water ad 100
9 N-methyl-N-(2-hydroxyethyl)-N,N-di-(tallowacyloxy-
ethyl)-ammonium methosulfate (90% active substance
in isopropanol) (STEPAN)
4) Hair rinse
STENOL~1618 2.5
EUMULGIN~B 1 1.0
EUMULGIN~B 2 1.0
EUTANOL~G 0.5
POLAWAX~GP 200ll 0.75
ABIL~QUAT 3270l2 0.5
DOW CORNING~929-Emulsionl3 2.6
Polymer JR0400l4 0.6
Polymer Pl acc. to DE 39 29 973 0.4

2139~95
. .
H 470 PCT 19
Citric acid 0.02
Water ad 100
~ Ester of saturated long-chain fatty alcohols and
fatty acids, primarily palmitic acid cetyl ester
(CTFA name: Cetyl Palmitate) (HENKEL)
Stearyl alcohol/polyethylene glycol stearate mix-
ture (CTFA name: Stearyl Alcohol (and) PEG
Stearate) (CRODA)
0 12 Diquaternary polymethyl siloxane (CTFA name: Qua-
ternium 80) (GOLDSCHMIDT)
3 Aminofunctional polydimethyl siloxane (35% active
substance) (DOW CORNING)
14 Quaternized hydroxyethyl cellulose (CTFA name:
Polyquaternium-10) (UNION CARBIDE)
5) Hair rinse
REWOQUAT~W 750015 1 . 1
LANETTE~0l6 3.0
EUMULGIN~B 1 0.8
EUMULGIN~B 2 1.6
CUTINA~GMS 0.5
EUTANOL~G 1.0
Polymer JR~40014 1.0
Polymer Pl acc. to DE 39 29 973 0.4
Water ad 100
5 1-Methyl-2-nortallowalkyl-3-tallow fatty acid
amidoethyl imidazolinium methosulfate (approx. 75%
active substance) (REWO)
16 Mixture of higher saturated fatty alcohols, pri-
marily cetyl and stearyl alcohol (CTFA name:
Cetearyl Alcohol (HENKEL)
17 Quaternized hydroxyethyl cellulose (CTFA name:
Polyquaternium-10) (UNION CARBIDE)

213999~
H 470 PCT 20
6) 8h~mpoo
TEXAPON~N 25~ 43.0
DEHYToN'DKI9 10 . O
PLANTAREN0-12002 4.0
S EUPERLAN~PK 300021 1.6
ARQUAD~316n 0.5
CELQUAT~L 200 1.2
Polymer P1 acc. to DE 39 29 973 0.2
GLUCAMATE~DOE 12023 0.5
Sodium chloride 0.2
Water ad 100
18 Sodium lauryl ether sulfate (approx. 28% active
substance; CTFA name: Sodium Laureth Sulfate)
(HENKEL)
~9 Fatty acid amide derivative, betaine structure,
corresponding to the formula R-CONH(CH2)3N+(CH3)2-
CH2COO- (approx. 30% active substance; CTFA name:
Cocoamidopropyl Betaine) (HENKEL)
20 C12-C16 alkyl glucoside, degree of oligomerization
1.4 (approx. 50% active substance; CTFA name:
Lauryl Polyglycoside (HENKEL)
21 Liquid dispersion of pearlescing substances and
amphosurfactant (approx. 62% active substance;
CTFA name: Glycol Distearate (and) Glycerin (and)
Laureth-4 (and) Cocoamidopropyl Betaine) (HENKEL)
22 Tri-C16-alkyl methyl ammonium chloride (AKZO)
23 Ethoxylated methyl glucoside dioleate (CTFA name:
PEG-120 Methyl Glucose Dioleate) (AMERCHOL)
7) 8hampoo
TEXAPON~N 70~ 21.0
PLANTAREN~-1200 8.0
GENAMIN~DSAC~ 1.2
CUTINA~EGMS26 0.6

~1~9495
H 470 PCT 21
Polymer JR04Ool4 0.8
Polymer Pl acc. to DE 39 29 973 O.3
ANTIL0141 liquid~ 1.3
Sodium chloride 0.2
Water ad lOO
Sodium lauryl ether sulfate (approx. 72% active
substance (~:NK~)
~ Dimethyl distearyl ammonium chloride (HOECHST)
26 Ethylene glycol monostearate (approx. 25-35% mono-
ester, 60-70% diester; CTFA name: Glycol Stearate)
(HE~KEL)
n Polyoxyethylene propylene glycol dioleate (40%
active substance; CTFA Name: Propylene Glycol
(and) PEG-55 Propylene Glycol Oleate)
(GOLDSCHMIDT)
8) 8h~mpoo
TEXAPON0K 14 S28 50.0
DEHYTON0K lO.O
AKYPO~RLM lOO NV29 4.5
CUTINA0AGS~ 2.0
D-Panthenol 0.5
Glucose l.O
Salicylic acid 0.4
Sodium chloride O.5
Polymer P1 acc. to DE 39 29 9730.6
CELQUAT0L 200 0.6
Water ad lOO
28 Sodium lauryl myristyl ether sulfate (approx. 28%
active substance; CTFA name: Sodium Myreth Sul-
fate) (~NK~I)
29 C12-14 fatty alcohol+lO ethylene oxide acetic acid
sodium salt (22% active substance; CTFA name:

2139~9S
.
H 470 PCT 22
Sodium Laureth-ll Carboxylate) (CHEM-Y)
30 Ethylene glycol stearate (approx. 5-15% monoester,
85-95g6 diester; CTFA name: Glycol Distearate)
(HENKEL)
9) 8h~mpoo
TEXAPON~9K 14 S 25.0
TEXAPONDSB 32~ 7-5
EUCARoL~TA32 12.0
AKYPO~RLM 100 NV 9.0
DEHYTONI9AB 3033 8.3
ELFACOS0GT 282S34 0-5
Sodium chloride 0.5
Polymer Pl acc. to DE 39 29 973 0.6
Polymer JR'19400l4 2.0
Water ad100
3~ Sulfosuccinic acid semiester based on an alkyl
polyglycol ether, di-Na salt (approx. 40% active
substance; CTFA name: Disodium Laureth Sulfosuc-
cinate) (HENKEL)
32 Lauryl alcohol+7 ethylene oxide tartrate sodium
salt (approx. 25% active substance; CTFA name:
Sodium Laureth-7 Tartrate) (AUSICHEM)
25 33 Fatty amine derivative, betaine structure (approx.
30% active substance; CTFA name: Coco-Betaine)
(HENKEL)
34 Tallow alcohol+60 ethylene oxide myristyl ether
(CTFA name: Talloweth-60 Myristyl Glycol) (AKZO)
10) Tonic pack (removable by rinsing)
STENOLI91618 3-
EUMULGIN~B 1 0-5
EUMULGIN~B 2 0.5
CUTINA0CP 1.0

~139495
H 470 PCT 23
EU'rANOl~G 1.5
CARBoPoL~98035 0.004
DOW COkhlNG~929 Emulsion 2.9
Polymer P1 acc. to DE 39 29 973 0.3
CEI.QUAT~L200 2.0
Triethanolamine o.og
Water ad 100
3~ Polyacrylic acid (GOODRICH)
11) To~ia paclc ~r~a~n~n~ on th- ~air)
CELQUAT~L 200 0.6
1WISKOL~K3036 0.2
D-Panthenol O.5
DEHYQUART~SP7 1.0
NUT~T~
NATROSO1'~'250 HR39 1.1
Polymer Pl acc. to DE 39 29 973 o.5
Water ad 100
36 Polyvinyl pyrrolidone (95% actiYe substance; CTFA
name: PVP) (BASF)
3~ Aqueous solution of hydroxyethyl alkylammonium
phosphate (approx. 50% active substance; CTFA
name: Quaternium-52) (n~;NK~;L)
3~ Collagen hydrolyzate (approx. 39% active subs-
tance; CTFA name: Hydrolyzed Collagen) (HENKEL)
39 Hydroxyethyl cellulose (AQUALON)
30 12) D~eing cre~
C12,1~ Fatty alcohol 1.2
k ~ 0 4 . O
~IN~B 2 0.8
~;ull~A~ RD 164 2.0
Sodium sulfite 0.5
:

213949~
H 470 PCT 24
L(+) Ascorbic acid 0.5
Ammonium sulfate 0.5
1,2-Propylene glycol 1.2
p-Aminophenol 0.35
p-Tolylene diamine 0.85
2-Methyl resorcinol 0.14
6-Methyl-m-aminophenol 0.42
Polymer Pl acc. to DE 39 29 973 0.5
CELQUAT0L 200 4.0
Ammonia 1.5
Water ad 100
Fatty acid mono/diglyceride emulsifier mixture
(CTFA name: Tallow Glycerides (and) Glyceryl
Stearate (and) Potassium Stearate) (HENKEL)
13) Developer dispersion for dyeing creAm 12)
TEXAPON0N 25 2.1
Hydrogen peroxide (50~) 12.0
TURPINAl0SL4l 1.7
LATEKoLL0D42 12.0
Polymer P1 acc. to DE 39 29 973 0.1
Polymer JR0 400 0.1
Water ad 100
41 1-Hydroxyethane-l,l-diphosphonic acid (60% active
substance; CTFA name: Etidronic Acid) (HENKEL)
44 Acrylate/methacrylic acid copolymer (25% active
substance) (BASF)
The dyeing cream had a pH value of 10Ø It gave
the hair a strong red tint.
14) Tinting shampoo
TEXAPON~N 70 14.0

213949S
H 470 PCT 25
DEHYTON~K 10.0
AKYPO~RLM 45 NV43 14.7
PLANTAREN~-1200 4.0
CREMOPHOR~RH 4046 0.8
Dye C.I. 12 719 0.02
Dye C.I. 12 251 0.02
Dye C.I. 12 250 0.04
Dye C.I. 56 059 0.03
PHB ester 0.25
CELQUAT~L200 0.8
Polymer Pl acc. to DE 39 29 973 0.2
Perfume oil q.s.
Water ad 100
5 43 Lauryl alcohol+4.5 ethylene oxide acetic acid
sodium salt (20.4% active substance) (CHEM-Y)
44 Castor oil, hydrogenated + 45 ethylene oxide (CTFA
name: PEG-40 Hydrogenated Castor Oil) (BASF)
When the hair was washed with this tinting
shampoo, it was left bright light blond in color.
15) Permanent wave cream
Wave cream
PLANTAREN~-80045 5.0
Thioglycoltc acid 8.0
TURPINAL~SL 0.5
Ammonia (25%) 7.3
Ammonium carbonate 3.0
Cetostearyl alcohol 5.0
Guerbet alcohol 4.0
CELQUAT~L200 1.2
Polymer P1 acc. to DE 39 29 973 0.1
Perfume oil q.s.
Water ad 100

,, . . ~139~9s
H 470 PCT 26
C8-C~0 alkyl glucoside, degree of oligomerization
1.6 (approx. 60~ active substance) (HENKEL)
Fixinq solution
PLANTAREN~-800 5.0
Hydrogenated castor oil 2.0
Potassium bromate 3.5
Nitrilotriacetic acid 0.3
Citric acid 0.2
Polymer Pl acc. to DE 39 29 973 0.2
Polymer JR~ 400 1.0
Perfume oil q.S-
Water ad 100

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Administrative Status

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Event History

Description Date
Inactive: IPC deactivated 2011-07-27
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: First IPC derived 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Inactive: IPC from MCD 2006-03-11
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2001-06-26
Inactive: Dead - RFE never made 2001-06-26
Application Not Reinstated by Deadline 2001-06-26
Inactive: Abandon-RFE+Late fee unpaid-Correspondence sent 2000-06-27
Application Published (Open to Public Inspection) 1994-01-20

Abandonment History

Abandonment Date Reason Reinstatement Date
2001-06-26

Maintenance Fee

The last payment was received on 2000-05-17

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
  • the late payment fee; or
  • additional fee to reverse deemed expiry.

Patent fees are adjusted on the 1st of January every year. The amounts above are the current amounts if received by December 31 of the current year.
Please refer to the CIPO Patent Fees web page to see all current fee amounts.

Fee History

Fee Type Anniversary Year Due Date Paid Date
MF (application, 5th anniv.) - standard 05 1998-06-24 1998-05-15
MF (application, 6th anniv.) - standard 06 1999-06-24 1999-05-19
MF (application, 7th anniv.) - standard 07 2000-06-27 2000-05-17
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN
Past Owners on Record
CHRISTIAN PRIEBE
DETLEF HOLLENBERG
KURT SEIDEL
REINHARD MUELLER
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Description 1994-01-19 26 887
Abstract 1994-01-19 1 8
Claims 1994-01-19 3 91
Reminder - Request for Examination 2000-02-27 1 119
Courtesy - Abandonment Letter (Request for Examination) 2000-08-07 1 172
Courtesy - Abandonment Letter (Maintenance Fee) 2001-07-23 1 182
Correspondence 2001-05-08 5 183
Fees 1997-05-21 1 61
Fees 1996-05-27 1 48
Fees 1995-01-02 1 30
International preliminary examination report 1995-01-02 56 1,666