Note: Descriptions are shown in the official language in which they were submitted.
`~ 21 ~3~7~
WO 92/13512 1 PCT/EP92/00179
A free-flowing pearle-Qcent concentrate
This invention relates to a pearlescent concen-
trate in the form of a free-flowing or pumpable, aqueous
dispersion containing 15 to 40% by weight pearlescing
components.
Aqueous preparations of surfactants and cosmetic
preparations can be given a pearlescent, aesthetically
attractive appearance by incorporation of substances
which, after cooling, precipitate in the form of fine
nacreous-looking crystals and remain dispersed in the
preparations. Suitable so-called pearlescers are, for
example, the monoesters, diesters and optionally tri-
esters of ethylene glycol, propylene glycol and oligo-
meric alkylene glycols of this type or glycerol with
C1422 fatty acids, fatty acids and also monoalkanolamides
of fatty acids.
It is also known that the pearlescers mentioned
form stable dispersions in water or in aqueous surfac-
tant solutions and that the concentrated pearlescent
dispersions obtained in this way can be added without
heating to the preparations to be given a pearlescent
appearance, so that there is no longer any need for the
heating and cooling otherwise necessary for incorpora-
tion to form the pearlescent crystals.
Pearlescent concentrates based on the pearlescers
mentioned above are known, for example, from DE-A-16 69
152, from JP-S6/71021 (Chem. Abstr. 95/156360), from DE-
A-34 11 328, DE-A-35 19 08~ and DE-A-38 43 5~2.
One problem affecting the production and use of
pearlescent concentrates concerns their flowability and
pumpability. Flowability and pumpability are often
seriously restricted, above all at high concentrations
of pearlescing components, or the mixtures present can-
21;33~73
Wo 92/13512 2 PCT/EP92/00179
not flow at all or cannot even be pumped by conventional
pumping equipment.
Accordingly, it was proposed in German patent
application D~ 38 ~3 572 to reduce the viscosity of
pearlescent concentrates by addition of small quantities
of low molecular weight, polyhydric alcohols and thus to
establish flowability and pumpability.
In addition, known pearlescent concentrates are
provided with preservatives, such as for example organic
acids (formic acid, benzoic acid, salicylic acid, sorbic
acid), formaldehyde, isothiazolinones, PHB esters or
1,3-dioxanes for protection against bacterial and fungal
contamination.
However, preservatives are known from dermatolog-
ical st-ldies to cause a number of skin irritations and
complaints. Accordingly, preservative-free personal
hygiene preparations and cosmetics have very recently
come increasingly onto the mar~et. To enable products
such as these to be given the asethetically attractive
appearance required by the consumer through the use of
pearlescent concentrates, there is thus a need for
pearlescent concentrates which can be formulated without
preservatives. However, the absence of preservatives
should not adversely affect the microbiological stabili-
ty or other properties of these concentrates.
It has now been found that preservative-free
pearlescent concentrates equivalent to known pearlescent
concentrates in their stability and in their flowability
and pumpability can be obtained by addition of relative-
ly large quantities of low molecular weight polyhydricalcohols.
Accordingly, the present invention relates to a
pearlescent concentrate in the form of a free-flowing,
aqueous dispersion which is characterized by a content
of
21~3~v73
Wo 92/13512 3 PCT/EP92/00179
(A) 15 to 40~ by weight pearlescing components,
(B) 5 to 55% by weight emulsifiers and
(C) 15 to 40% by weight low molecular weight, poly-
hydric alcohols.
Particularly advantageous properties are exhi-
bited by pearlescent concentrates containing
(A) 20 to 30% by weight pearlescing components,
(B) 10 to 35% by weight emulsifiers and
(C) 20 to 40% by weight low molecular weight, poly-
hydric alcohols.
Pearlescing components are understood to be
fusible fats or waxes which crystallize out in the form
of fine, pearlescing substances on cooling of their
aqueous solutions or emulsions at temperatures in the
range from about 30 to 90C.
These fusible fats or waxes include
(Al) esters corresponding to formula (I)
R - (CnH2n)~ - OR (I)
in which Rl is a linear C1422 fatty acyl group, R2
is hydrogen or a group R1, n = 2 or 3 and x is a
number of 1 to 4,
(A2) monoalkanolamides corresponding to general
formula (II)
R3 - CO - NH - X (II)
in which R3 is an alkyl group containing 8 to 22
and, more especially, 8 to 18 carbon atoms and X
is a -CH2-CHz-OH group, a -CH2-CH2-CH2-OH group or
21 ~3~73
wo 92/13512 4 PCT/EP92/00179
a -C(CH3)2-OH group,
(A3) linear, saturated C1~22 fatty acids and
(A4) B-ketosulfones corresponding to general formula
(III):
Rs
R4 - CO - CH - SO2 - CH2 - R6 (III)
.
in which R4 is a C112l alkyl or alkenyl group, R5
and ~6 are hydrogen atoms or together represent an
ethylene group which forms a tetrahydrothiophene
dioxide ring with the group between R5 and R6 and
(A5) mono-, di- and triesters of glycerol with linear
saturated C1~22 fatty acids.
Suitable esters (A1) corresponding to the general
formula Rl(O~H2n)~OR2 are, for example, the monoesters and
diesters of ethylene glycol and propylene glycol with
higher fatty acids, for example with palmitic acid,
stearic acid or behenic acid, or the diesters of diethy-
lene glycol or triethylene glycol with such fatty acids.
Also suitable are mixtures of monoesters and diesters of
the glycols mentioned with fatty acid mixtures, for
example with hydrogenated tallow fatty acid, palm oil
fatty acid or with the saturated C1~18 fatty acid frac-
tion of tallow fatty acid. The ethylene glycol mono-
ester and/or diester of palmitic and/or stearic acid is
particularly suitable.
Preferred monoalkanolamides (A2) are the mono-
ethanolamides. These compounds may contain individual
alkyl radicals. However, it is standard practice to
produce the alkanolamides from fa~ty acid mixtures from
natural sources, for example coconut oil fatty acids, so
that corresponding mixtures are present in regard to the
alkyl radicals.
21~3~73
~o 92/13512 5 PCT/EP92/00~79
Suitable linear fatty acids (A3) are, for ex-
ample, palmitic acid, stearic acid, arachic acid or
behenic acid, although it is also possible to use
technical fatty acid cuts consisting entirely or predom-
inantly of C162z fatty acids, for example palmitic/
stearic acid fractions of the type obtained from tallow
fatty acid or palm oil fatty acid by separation of the
fatty acids liquid at +5 C or palmitic/stearic acid
fractions of the type obtainable by hydrogenation of
tallow fatty acid or palm oil fatty acid.
The ~-ketosulfones (A4) of general formula (III)
have the advantage over the known ethylene glycol
monoesters and diesters that the pearlescence of the
preparations shows higher heat stability, i.e. the
preparations retain their pearlescence for several hours
on heating to temperatures above 50 C and, in some
cases, to temperatures above 70-C. Further information
on the B-ketosulfones mentioned can be found in German
patent application 35 08 051.
The esters of glycerol (A5) suitable for use in
accordance with the teaching of the invention include
the mono-, di- and in particular triesters with myristic
acid, palmitic acid, stearic acid and behenic acid and
with mixtures of these fatty acids.
Fatty alcohols containing at least 20 C atoms
and, in particular, 20 to 30 C atoms may also be used as
pearlescing components.
The pearlescent concentrates according to the
invention may exclusively comprise representatives of
one of these classes of compounds and also mixtures of
representatives of several of these classes of com-
pounds.
Preferred pearlescing components are representa-
tives of classes (Al) to (A3).
However, fatty acid mono- or dialkanolamides,
- 2 1 ~ 3 ~ ~ ~
~o 92/13512 6 PCT/EP92/00179
i.e. pearlescing components of group (A2), and deriva-
tives thereof have recently been suspected of partici-
pating in the formation of nitroamines. Accordingly, it
may be desirable to formulate cosmetic preparations
without such alkanolamines and alkanolamine derivatives.
For this reason, compounds of classes (A1) and (A3) can
be particularly preferred pearlescing components.
Pearlescent concentrates in which at least 70% by
weight and more especially at least 9o~ by weight of the
pearlescing components consist of ethylene qlycol
distearate are particularly preferred.
Emulsifiers (B) are ionic or nonionic surface-
active compounds distinguished by a lipophilic, prefer-
ably linear, alkyl or alkenyl group and at least one
hydrophilic group. The hydrophilic group may be both an
ionic group and also a nonionic group.
Suitable anionic emulsifiers (B) suitable for use
in accordance with the invention are, for example, alkyl
sulfates and alkyl polyethylene glycol ether sulfates
containing 8 to 22 C atoms in the alkyl chain and 1 to
15 and more particularly 1 to 6 ethylene glycol ether
groups in the molecule which are used in the form of
their alkali, magnesium, ammonium, mono-, di- or tri-
alkanolammonium salts containing 2 to 3 C atoms in the
alkanol group. Other suitable anionic surfactants are
alkanesulfonates, ~-olefin sulfonates, ~-sulfofatty acid
methyl esters, fatty alcohol (polyglycol ether) carboxy-
lates, sulfosuccinic acid mono- and dialkyl esters, sul-
fosuccinic acid ester salts, acyl isethionates, acyl
taurides and acyl sarcosides containing 8 to 22 and more
particularly 12 to 18 C atoms in the alkyl or acyl
chain. Soaps may also be used as emulsifiers. This may
~e achieved, for example, by saponifying a small propor-
tion, for example about 1 to 20% by weight, of the
linear, saturated fatty acids by added alkali metal
21~3.78
~O 92/13512 7 PC~/EP92/0017g
hydroxide and thus converting it into an anionic emul-
sifier.
Preferred anionic emulsifiers are the alkyl
polyethylene glycol ether sulfates such as, for example,
sodium lauryl polyglycol ether sulfate.
Suitable cationic emulsifiers (B) are quaternary
ammonium surfactants, for example alkyl trimethyl
ammonium chlorides and dialkyl dimethyl ammonium chlo-
rides, for example cetyl trimethyl ammonium chloride,
stearyl trimethyl ammonium chloride, distearyl dimethyl
ammonium chloride, lauryl dimethyl ammonium chloride and
lauryl dimethyl benzyl ammonium chloride, cetyl pyri-
dinium chioride and tallow alkyl tris-(oligooxyalkyl)-
ammonium phosphate.
Zwitterionic surfactants may also be used as the
emulsifiers (B). 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
surfactants are the so-called betaines, such as the N-
alkyl-N,N-dimethyl ammonium glycinates, for example
cocoalkyl dimethyl ammonium glycinate, N-acylamino-
propyl-N,N-dimethyl ammonium glycinates, for example
cocoacylaminopropyl dimethyl ammonium glycinate, and 2-
alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines
containing 8 to 18 carbon atoms in the alkyl or acyl
group and also cocoacylaminoethyl hydroxyethyl car-
boxymethyl glycinate. The fatty acid amide derivative
known by the CTFA name of cocoamidopropyl betaine is a
preferred zwitterionic surfactant.
Other suitable emulsifiers (B) are ampholytic
surfactants. Ampholytic surfactants are surface-active
compounds which, in addition to a C8l8 alkyl or acyl
group in the molecule, contain at least one free amino
group and at least one -COOH or -SO3H group and are
` 21i33~7~
~o 92/13512 8 PC~/EP92/00179
capable of forming inner salts. Examples of suitable
ampholytic surfactants are N-alkyl glycines, N-alkylpro-
pionic acids, N-alkylaminobutyric acids, N-alkylimino-
dipropionic acids, N-hydroxyethyl-N-alkylamidopropyl
glycines, N-alkyltaurines, N-alkylsarcosines, 2-alkyl-
aminopropionic acids and alkylaminoacetic acids contain-
ing approximately 8 to 18 carbon atoms in the alkyl
group. Particularly preferred ampholytic surfactants
are N-cocoalkylaminopropionate, cocoacylaminoethylamine
propionate and C~218 acyl sarcosine.
Finally, it is also possible to use nonionic
emulsifiers (B) which contain, for example, a polyol
group, a polyalkylene glycol ether group or a combina-
tion of a polyol group and a polyglycol ether group as
the hydrophilic group. Compounds such as these are, for
example,
(B1) adducts of 2 to 30 mol ethylene oxide and/or 0 to
5 mol propylene oxide with linear Ca22 fatty
alcohols, with C1222 fatty acids and with alkyl
phenols containing 8 to 15 carbon atoms in the
alkyl group,
(B2) C~222 fatty acid monoesters and diesters of
adducts of 1 to 30 mol ethylene oxide with
glycerol,
(B3) glycerol monoesters and diesters and sorbitan
monoesters and diesters of saturated and unsatu-
rated Ca22 fatty acids and ethylene oxide adducts
thereof,
(B4) C822 alkyl mono- and -oligoglycosides and ethoxy-
lated analogs thereof and
(B5) adducts of 10 to 60 mol ethylene oxide with
castor oil and hydrogenated castor oil.
Mixtures of compounds from several of these
` h~ 33~7d
W0 92/13512 9 PCT/E~92/00179
classes are also suitable.
The adducts of ethylene oxide and/or propylene
oxide with fatty alcohols, fatty acids, alkyl phenols,
glycerol monoesters and diesters and sorbitan monoesters
and diesters of fatty acids or with castor oil are known
commercially available products. They are homolog
mixtures of which the average degree of alkoxylation
corresponds to the ratio between the quantities of
ethylene oxide and/or propylene oxide and substrate with
which the addition reaction is carried out.
C~222 fatty acid monoesters and diesters of
adducts of ethylene oxide with glycerol are known from
DB-PS 20 24 051 as refatting agents for cosmetic prepar-
ations. C822 alkyl mono- and -oligoglycosides, their
production and their use as surfactants are known, for
example, from ~S-A 3,839,318, US-A 3,707,535, US-A
3,547,828, DE-A 19 43 689, DE-A 20 36 472 and DE-A 30 01
064 and from EP-A 77 167. They are prepared in particu-
lar by reaction of glucose or oligosaccharides with
primary C322 alcohols. So far as the glycoside residue
is concerned, both monoglycosides, in which a cyclic
sugar residue is attached to the fatty alcohol by a
glycoside bond, and also oligomeric glycosides having a
degree of oligomerization of up to, preferably, about 8
2S are suitable. Degrees of oligomerization of 1.4 and
lower can be particularly preferred. The degree of
oligomerization is a statistical mean value on which a
homolog distribution typical of such technical products
is based.
The compounds of group (Bl) are particularly
preferred nonionic emulsifiers (~) for the purposes of
the invention.
The compounds containing alkyl groups used as
surfactants may be individual substances. However, it
is generally preferred to use native vegetable and
21~ 7~
~o 92/13512 10 PCT/EP92/00179
animal starting materials in the production of these
compounds, sc that mixtures having different alkyl chain
lengths depending on the particular starting material
used are obtained.
The surfactants which are adducts of ethylene
and/or propylene oxide with fatty alcohols may be both
products with a "normal" homolog distribution and
products with a "narrow" homolog distribution. Products
with a "normal" homolog distribution are understood to
be 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 homolog
distributions are obtained when, for example, hydrotal-
lS cites, alkaline earth metal salts of ether carboxylic
acids, alkaline earth metal oxides, hydroxides or
alcoholates are used as catalysts. The use of so-called
"narrow-range" products can be preferred.
According to the teaching of the invention, the
pearlescent concentrates may contain representatives of
one or more of the surfactant classes mentioned.
Since pearlescent concentrates are mainly added
to formulations containing anionic surfactants, anionic
emulsifiers are preferred emulsifiers (B).
In addition, the pearlescent concentrates accord-
ing to the invention, which contain only nonionic,
zwitterionic and/or ampholytic surfactants, have proved
to be particularly universally usable and to be partic-
ularly compatible with water-cor.taining preparations of
water-soluble surfactants of any type and any ionicity.
Accordingly, the use of surfactants from these classes
is also preferred.
The presence of low molecular weight polyhydric
alcohols is crucial to the flowability or pumpability of
the pearlescent concentrates according to the invention
t
21 U3~7~
WO ~2/13512 11 PC~/EP92/00179
and also to their resistance to bacterial and fungal
contamination.
Preferred low molecular weight polyhydric al-
cohols contain 2 to 6 carbon atoms and 2 to 6 hydroxyl
groups. Alcohols such as these are, for example,
ethylene glycol, 1,2- and 1,3-propylene glycol, glycer-
ol, di- and triethylene glycol, erythritol, arabitol,
adonitol, xylitol, sorbitol, mannitol and dulcitol. It
is particularly preferred to use glycerol, 1,2-propylene
glycol, 1,3-propylene glycol and/or sorbitol.
The use of glycerol as the low molecular weight
polyhydric alcohol leads to pearlescent concentrates
which give the end products a particularly brilliant
pearlescenceO
In addition to the components mentioned above,
the pearlescent concentrates according to the invention
essentially contain water.
In addition, the concentrates may contain small
quantities of buffers to adjust the pH to values in the
range from 2 to 8, for example citric acid and/or sodium
citrate, and also inorganic salts, for example sodium
chloride, as thickener.
Although the pearlescent concentrates are normal-
ly free from preservatives, small quantities of commer-
cially available preservatives - introduced for example
through certain starting materials - may be present in
exceptional cases.
The pearlescent concentrates according to the
invention are pumpable at least over a temperature range
of 5 to 40'C and remain stable in storage for prolonged
periods, i.e. for at least about 3 months.
The pearlescent concentrates according to the
invention are preferably prepared by initially heating
components (A), (B) and (C) together to a temperature
approximately 1 to 30-C above the melting point. In
2~ i3~7~
WO 92/13512 12 PCT/EP92/00179
most cases, this will be a temperature in the range from
about 60 to 90-C. The water heated to substantially the
same temperature is then added to this mixture. Where
an ionic water-soluble surfactant is used as the emul-
sifier, it may be preferred to dissolve it in the
aqueous phase and to introduce it together with the
water into the mixture. The aqueous phase may even
already contain the buffer substances in dissolved form.
The dispersion formed is then cooled with continuous
stirring to room temperature, i.e. to around 251C. In
most cases, the viscosity of the pearlescent concentrate
is so low that there is no need to use special stirring
units, such as homogenizers or other high-speed mixers.
The pearlescent concentrates according to the
invention are suitable for the production of clouded and
pearlescent, liquid aqueous preparations of water-solu-
ble surfactants. They may be incorporated, for example,
in liquid detergents, such as dishwashing detergents,
liquid light-duty detergents and liquid soaps but are
preferably incorporated in liquid personal hygiene and
body-care preparations, such as for example shampoos,
liquid hand and body soaps, shower bath preparations,
bath additives (foam baths), hair rinses or hair dyes.
To produce pearlescence, the pearlescent concen-
trates according to the invention are added to the clear
aqueous preparations at 0 to 40 C in a quantity of 1 to
10% by weight and more especially in a quantity of 1.5
to 5% by weight of the preparation and are dispersed
therein with stirring. A metallic, dense to slightly
lustrous, extremely dense pearlescence is obtained, t
depending on the preparation and the concentration used.
The following Examples are intended to illustrate
the invention without limiting it in any way.
21~3~
WQ 92/13512 13 PCT/EP92/00179
Examples
1. Pearlescent concentrates
Pearlescent concentrates having the compositions
shown in Table 1 were prepared. The components shown
in the form of trade names are the following substances:
Ethylene glycol distearate (at least 90% diester)
(HENKEL)
2 Coconut oil fatty acid monoethanolamide (CTFA
name: Cocamide MEA (approx. 95% amide)) (HENKEL)
C~mposition of the fatty acid:
approx. 56% lauric acid
approx. 21% myristic acid
approx. 10% palmitic acid
approx. 13% stearic acid and oleic acid
3 Palmitic/stearic acid mixture (approx. 1:1)
4 Fatty alcohol polyglycol ether (CTFA name:
Laureth-10 (approx. 74% C12~l~ fatty alcohol))
(HENKEL)
Sodium lauryl ether sulfate (CTFA name: Sodium
Laureth Sulfate (approx. 72% active substance))
(HENKEL)
6 Clz_l4 fatty alcohol + 4 ethylene oxide (HENKEL)
Aqueous solution of a fatty acid amide derivative
of betaine structure having the formula
R-CONH-(CH2)3-N+( C~3 )2-CH2-COO (CTFA name Cocamido-
propyl Betaine (approx. 30% active substance,
approx. 5% NaCl)) (HENKEL)
21 ~33~7~
PCT/EP92Jo0179
Wo 92/13512 14
8 C~2l~ fatty alcohol + 3 ethylene oxide (HENKEL)
9 Polyol fatty acid ester (CTFA name: PEG-7-Gly-
ceryl Cocoate) (HENKEL)
86% Water
N 2 1 ~ 3 ~ 7 ~
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WO 92/1~512 16 PCT/EP92/00179
Application Examples
l) Shower bath
Parts by weight
Texapon~R~N25l1 35
Dehyton(R)K 7
Lamepon~R~Sl2 5
Pearlescent concentrate l 3
Water ad 100
The viscosity of the shower bath was then adjusted to
4,000 mPas by addition of sodium chloride.
11 Sodium lauryl ether sulfate (CTFA name: Sodium
Laureth Sulfate (approx. 28% active substance in
water) (HENREL)
12 Protein hydrolyzate fatty acid condensate potassium
salt (CTFA name: Potassium Coco-Hydrolyzed Animal
Collagen) (HENREL)
2) Mild shampoo
Parts by weight
Texapon(R)ASV13 14
Texapon(R~SB 3~4 10
Dehyton~R~G15 14
Nutrilan(R)I S016 2.5
Pearlescent concentrate 2 2
Water ad 100
The viscosity was then adjusted to S,000 mPas by
addition of sodium chloride and Arlypon(R~F (narrow-range
ethoxylated fatty alcohol) (HENKEL)).
2~ 33~7~
W0 92~13512 17 PCT/EP92/00179
13 A mixture of special fatty alcohol ether sulfates
(CTFA name: Sodium Laureth Sulfate (and) Magnesium
Laureth Sulfate (and) Sodium Laureth 8-Sulfate (and)
Magnesium Laureth 8-sulfate ~and~ Sodium Oleth
Sulfate (and) Magnesium Oleth Sulfate (approx. 30
active substance in water)) (HENKEL)
Sulfosuccinic acid semiester based on an alkyl
polyglycol ether, di Na salt (CTFA name: disodium
laureth sulfosuccinate (approx. 40% active substance
in water)) (HENKEL)
15 Amphoteric fatty acid amide derivative (N-hydroxy-
ethyl-N-cocoalkylamidoethyl glycinate, Na salt) (CTFA
name: Cocoamphodiacetate (approx. 30~ active sub-
stance in water)) (HENKEL)
16 Partial protein hydrolyzate of degraded bovine
collagen (CTFA name: Hydrolyzed Animal Protein)
(HENKEL)
3) Foam bath
Parts by weight
Texapon(R~N 4017 40
Dehyton(R~K 6.5
Dehyton(R~G 6.5
Cetiol~R) HE 5
Pearlescent concentrate 3 5
Water ad 100
The viscosity was then adjusted to 6,000 mPas by
addition of sodium chloride.
17 Sodium lauryl ether sulfate (CTFA name: Sodium
Laureth Sulfate (approx. 28% active substance in
water)) (HENKEL)~
