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Patent 2064482 Summary

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(12) Patent Application: (11) CA 2064482
(54) English Title: USE OF ALKYLGLYCOSIDE SULFOSUCCINATES FOR THE PRODUCTION OF COSMETIC PREPARATIONS AND CLEANING AGENTS
(54) French Title: EMPLOI DE SULFOSUCCINATES D'ALKYLGLYCOSIDE POUR LA PREPARATION DE PRODUITS DE BEAUTE ET D'AGENTS DE NETTOYAGE
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11D 1/755 (2006.01)
  • C07H 15/04 (2006.01)
  • C07H 15/08 (2006.01)
  • C11D 1/12 (2006.01)
(72) Inventors :
  • HINTZ, MATHIAS (Germany)
  • KOHLE, HANS-JURGEN (Germany)
  • MOLLER, CHRISTL (Germany)
  • SALOMON, THOMAS (Germany)
  • WEIGAND, JOACHIM (Germany)
(73) Owners :
  • WITCO SURFACTANTS G.M.B.H. (Not Available)
(71) Applicants :
(74) Agent: MARKS & CLERK
(74) Associate agent:
(45) Issued:
(22) Filed Date: 1992-03-31
(41) Open to Public Inspection: 1992-10-05
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
P 41 10 852.3 Germany 1991-04-04

Abstracts

English Abstract


Abstract:

Use of alkvlalycoside sulfosuccinates for the production
of cosmetic preparations and cleaning agents


The invention relates to the use of
alkylglycoside sulfosuccinates of the general formula (1)


Image


R is a linear, saturated or unsaturated hydrocarbon
radical having 1 - 18 C atoms or


Image where R1 is H or R and x is 1 - 10
R2 is a linear, saturated or unsaturated acyl radical
having 8 - 22 C atoms
R3, independently of one another, are H and at least
once can be the radical
[CO-CH(SO3-)-CH2-COO-]2K+ and
R4, independently of one another, can be H or CH3
n is a number between 1 and 6 and

y1-4 can be 0 - 5, where
n(y1+y2+y4)+y3 = n(1-20)+y3, and
K+ is any desired cation of an alkali metal (Na),


- 36 -

alkaline earth metal, ammonium or H
for the production of cosmetic preparations.


Claims

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


- 30 -
THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. The use of alkylglycoside sulfosuccinates of the
general formula (1)
Image

R is a linear, saturated or unsaturated hydrocarbon
radical having 1 - 18 C atoms or

Image where R1 is H or R and x is 1 - 10
R2 is a linear, saturated or unsaturated acyl radical
having 8 - 22 C atoms
R3, independently of one another, are H and at least
once can be the radical
[CO-CH(SO3-)-CH2-COO-]2K+ and
R4, independently of one another, can be H or CH3
n is a number between 1 and 6 and
y1-4 can be 0 - 5, where
n(y1+y2+y4)+y3 = n(1-20)+Y3, and
K+ is any desired cation of an alkali metal (Na),
alkaline earth metal, ammonium or H


- 31 -

for the production of cosmetic preparations.
2. The use of alkylglycoside sulfosuccinates as
claimed in claim 1, wherein
R is an alkyl radical having 1 - 4 C atoms
R2 is an acyl radical of the mixture of natural coconut
fatty acids
R3, independently of one another, are H and at least
once can be the radical
(CO-CH(SO3-)-CH2-COO-]2X+ and
R4, independently of one another, can be H or CH3
n is 1 - 2
y1-4 is 0 - 5, where n(y1+y2+y4)+y3 = n(1-3)+y3
K+ is any desired cation of an alkali metal (Na),
alkaline earth metal, ammonium or H,
for the production of cosmetic preparations and cleaning
agents.
3. An aqueous preparation containing
A) 5 - 20 % by weight of at least one of the compounds
according to the general formula (1)

Image
R is a linear, saturatea or unsaturatea hydrocarbon
radical having 1 - 18 C atoms or

- 32 -
R4
-(CH2-CH-O)X-R1 where R1 is H or R and x is 1 - 10
R2 is a linear, saturated or unsaturated acyl
radical having 8 - 22 C atoms
R3,independently of one another, are H and at least
once can be the radical
[CO-CH(SO3-)-CH2-COO-]2K+ and
R4,independently of one another, can be H or CH3
n is a number between 1 and 6 and
y1-4 can be 0 - 5, where
n (y1+y2+y4)+y3 = n(1-20)+Y3, and
K+ is any desired cation of an alkali metal (Na),
alkaline earth metal, ammonium or H
B) 1 - 5 % by weight of at least one thickener
C) 0 - 10 % by weight of an electrolyte salt
D) 0 - 10 % by weight of customary auxiliaries and
additives
E) 55 - 94 % by weight of water.
4. An aqueous hair-cleaning agent, containing
a) 1 - 10 parts by weight of at least one of the
compounds of the general formula (1) and
b) 1 - 20 parts by weight of at least one surfactant
from the group comprising the nonionic,
amphoteric, zwitterionic or ionic surfactants and
optionally
c) 0.1 - 10 parts by weight of thickeners,
fragrances, preservatives, colorants, vegetable
extracts and other additives and auxiliaries and


- 33 -
d) water to 100.
5. An aqueous shower bath, containing
a) 1 - 10 parts by weight of the compounds of the
general formula (1)
b) 1 - 20 parts by weight of at least one nonionic,
amphoteric, zwitterionic or ionic surfactant and
c) 0.1 - 10 parts by weight of thickeners,
fragrances, preservatives, colorants, vegetable
extracts and other additives and auxiliaries and
optionally
d) water to 100.
6. An aqueous washing-up liquid, containing
a) 1 - 10 parts by weight of at least one of the
compounds of the general formula (1) and
b) 1 - 30 parts by weight of at least one surfactant
from the group comprising the nonionic,
amphoteric, zwitterionic and ionic surfactants
and optionally
c) 0.1 - 10 parts by weight of thickeners,
fragrances, preservatives, colorants, vegetable
extracts and other additives and auxiliaries and
optionally
d) water to 100.
7. A skin cream, containing
a) 1 - 10 parts by weight of at least one of the
compounds of the general formula (1) and
b) 1 - 10 parts by weight of at least one surfactant
from the group comprising the nonionic,


- 34 _
amphoteric, zwitterionic and ionic surfactants
and optionally
c) 0.5 - 20 parts by weight of vegetable or mineral
oils, or ester oils
d) 1 - 10 parts by weight of consistency-imparting
agent
e) 0.5 - 5 parts by weight of fragrances, colorants
or preservatives
f) water to 100.
8. A baby shampoo, containing
a) 1 - 10 parts by weight of at least one of the
compounds of the general formula (1) and
b) 0.1 - 20 parts by weight of at least one
surfactant from the group comprising the
nonionic, amphoteric, zwitterionic and ionic
surfactants and optionally
c) 0.1 - 10 parts by weight of thickeners,
fragrances, preservatives, colorants, vegetable
extracts and other additives and auxiliaries and
optionally
d) water to 100.


Description

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


~. 2~4~2

Use of alkylglvcoside sulfosuccinates for the ~roduction
of cosmetic pre~arations and cleanina agents
The invention relates to the use of alkoxylated
sulfosuccinates containing e~ter groups and based on
alkyl glycosides for the production of mild cosmetic
preparations and aqueous compositions which contain these
compounds.
Cosmetic preparations, in particular those which
come within the area of hair and body cleaning, such as
shower baths, foam baths, hair shampoos, baby shampoos,
baby baths and liquid soaps, contain as cleaning
components mainly anionic surfactants such as
carboxylates, alkyl sulfates and alkyl ether sulfates.
These preparations should clean the skin surface,
preferably only the film adhering to it, which can
consist of body secretions such as perspiration and fats,
flakes of skin or depo~ited dirt from the environment.
The cleaning agents should in no case dry out the skin,
irritate it or impair its natural function.
As the preparations can lead, however, during
their frequent - in recent years almost daily - use to
irritations of the skin, use is frequently additionally
made, in order to improve the skin and eye mucosa
compatibility, of so-called mild surfactants such as, for
example, betaines, protein derivatives, ampholytes, alkyl
ether carboxylates and sulfosuccinates.
Especially for baby care agents and baby shampoos
and preparations for sensitive skin, particular value is


2 ~ 8 2
-- 2 --


placed on extremely low contents of substances irrita~ing
the skin and eye mucosa. The anionic surfactants
conventionally used because of their excellent cleaning
and foam-forming properties can be rendered substantially
milder in their irritant action by means of the known
mild cosurfactants, but in practice improvements, in
particular in the way of eye mucosa compatibility, are
still required.
In high concentrations or on their own, the mild
surfactants are substantially irritation-free, but then
do not have foaming and cleaning properties suitable for
practical use and have unsatisfactory viscosities.
A further criterion for the utilizability of the
surface-active substances is their toxicity. The toxicity
lies in the surfactants themselves or products thereof
formed by interaction with the constituents of the
recipe.
As a result of increased environmental awareness,
products are additionally required which are based on
natural, renewable raw substances, have no toxicity
whatsoever and can be rapidly and completely degraded in
municipal sewage plants without toxic intermediates.
GB Patent 2,011,462 di~closes polyalkoxylated
mono- and dicarboxylates of ~-methylglucosides, the only
surfactant disclosed being GLUCAMATE-SSE-20 from Amerchol
- a mixture of the mono- and distearate of ~-methyl-
glucoside. It is used in ~kin-compatible preparations for
removing make-up from the eyes.


~ ~ 206~ 2
- 3 -


German Published Specification 3,336,760
describes mixtures of at least one oligomeric alkyl-
glucoside ether containing an alkyl radical having 8 - 10
C atoms, ethoxylated methylglucoside dioleate, alkyl- or
hydroxyalkyl polyglycosides containing an alkyl radical
having 11 - 18 C atoms and between 3 - 25 glycoside units
and at least one nonionic polymer from the group
comprising the alkyl celluloses, polyhydroxyalkyl
celluloses, poly-~-alanines and polyvinylpyrrolidone as
mild hair- and body-cleaning agents.
In practice, high molecular weight compounds
sometimes exhibit application problems: they are very
often difficult to dissolve in water and necessitate a
relatively large outlay on incorporation; occasionally it
is difficult to obtain the desired viscosity immediately
or the formulations tend to be "stringy" and produce a
sticky feeling on the skin. Some of these disadvantages
can be due to preparation and could possibly be overcome
by appropriate apparatus measures and careful monitoring
of the course of the process.
The ob~ect of the present invention is to
overcome these disadvantages of the prior art and to make
available mild, skin-compatible cosmetic preparations, in
particular those which come within the area of hair- and
body-cleaning.
This ob~ect is achieved by the alkoxylated
sulfosuccinates containing ester groups and based on
alkyl glycosides additionally used according to the


206~g~


invention. The invention therefore relates to the use of

alkylglycoside sulfosuccinates of the general formula (l)
Rq
C~2 -O- (CH~ -CH-~- ), 4 _~<2
r 1 1
;, (t~L~ H3 ) -n- ! -CH (: H-(~ ?.
/
C~ -- CH
L
R3 ~ 2 (OC2 H3 ) -~i o- (r2 H3
R4 R'
R is a linear, saturated or unsaturated hydrocarbon
radical having 1 - 18, preferably 1 - 10, in
particular 1 - 4 C atoms or



R4
-(CHz-CH-O)x-Rl where R1 iB H or R and x i8 1 - 1 0,
preferably 1 - 5.
R2 i8 a linear, saturated or unsaturated acyl radical
having 8 - 22 C atoms, preferably 12 - 18 C atoms
R3, independently of one another, are H and at least
once can be the radical
tCO-CH( S03- )-CH2-COO-]2R+ and
R4, independently of one another, can be H or CHa
n is a number between 1 and 6, preferably 1 and 3 and
y~ - 4 can be 0 - S, where
n (yl+yZ+y4 ) +y3 = n(1-20)+y3, preferably n(l-lO)+y3, in
particular n(1-3)+y3, and
R+ is any desired cation of an alkali metal (Na),
alkaline earth metal, ammonium or H


2~644~2
- 5 -


for the production of cosmetic preparations and cleaning
agents.
The invention further relates to aqueou~
preparation~ containing
A) 5 - 20 % by weight of at least one of the compounds
according to the general formula ~1) ?~

R 4




( CC: H J ) ~ ^ U _ r
I \, / !
! ;
R3Y2 (OC2r~ O ~-(C2:;3O)YI?.
I ~ R ~
R is a linear, saturated or unsaturated hydrocarbon
radical having 1 - 18, preferably 1 - 10, in
particular 1 - 4 C atom~ or
-(CH2-CH2-0)x-Rl where Rl i8 H or R and x i~
1 - 10, preferably 1 - 5.
R2 is a linear, saturated or unsaturated acyl
radical having 8 - 22 C atoms, preferably 12 - 18
C atoms
R3,independently of one another, are H and at lea~t
once can be the radical
[C0-CH(S03-)-CH2-C00-]2X~ and
R4,independently of one another, can be H or -CH3
n is a number between l and 6, preferably 1 and 3
and
yl~4 can be 0 - 5, where
n(yl+y2+y4)+y3= n(l-20)+y3, preferably n(l-lO)~y3,


~064~82
-- 6 --


~+ is any desired cation of an alkali metal (Na),
alkaline earth metal, ammonium or H
B) 1 - 5 % by weight of at least one thickener
C) O - 10 ~ by weight of an electrolyte salt
D) O - 10 % by weight of customar~ auxiliaries and
additives.
E) 55 - 94 ~ by weight of water.
Further embodiments of the invention are
characterized by the claims.
One starting substance for the preparation of the
additionally used compounds of the general formula (1)
according to the invention are commercial monomers and
oligomers of glucose, for example glucose syrup from
Cerestar.
The degree of polymerization of the glucose
varies according to the process and manufacturer and is
in the range 1 - 10 (n = 1 - 10), such that the compounds
according to the invention are also mixtures of these
various degrees of polymerization. Although the maximum
degree of polymerization i8 at n = about 10, the largest
part has a degree of polymerization (n~ of lesa than 5.
The mean value of n can therefore also be a decimal
number, that is to say lie between two integers.
The degrees of polymerization claimed according
to the invention of n = 1 to 6 therefore also comprise
the comparatively small amounts with values >6. Those
preferred according to the invention are degrees of
polymerization where n ~3 and in particular 1 - 2 with a


206~8~
-- 7


center around 1 - l.S.
These glycosides are etherified or
transetherified by generally customary processes (cf.
US Patent 4,704,453, EP-A-0,301,298).
The group R of the glycoside is preferably an
alkyl or alkenyl group having 1 - 10, in particular 1 -
4 C atoms, and can optionally be replaced by higher
groups having up to 18 C atoms. R can furthermore be a
polyether group of the structure -(CH2-CH2-O-~x-Rl, in
which R1 is H or R and x can assume values between 1 - 10,
preferably 1 - 5.
In a second step the reaction of one mol of fa~ty
acid or fatty acid methyl or fatty acid ethyl ester
respectively is carried out per glycoside unit. Instead
of the fatty acids or their methyl or ethyl esters, the
natural fats and oils, that is to ~ay their glycerol
esters, can also be employed.
The fatty acids used are the monobasic acids
having 8 - 22 C atoms - preferably the naturally
occurring acids - such as lauric acid, myristic acid,
palmitic acid, stearic acid, oleic acid, linoleic acid,
linolenic acid, ricinoleic acid, coconut fatty acid or
their mixtures (compare J. Am. Oil Chemists' Soc. 38, 517
- 520 (1961) and EP-A 0,190,779).
The glycoside esters are alkoxylated, preferably
ethoxylated or propoxylated, by processes known per se
(J. Am. Oil Chemists' Soc. 38, 517 - 520 (1961), US
Patent 3,640,998). The ethoxylation or propoxylation can




.


.

2~482


also be carried ou~ before the introduction of the ester
function. The amounts of ethylene oxide and/or propylene
oxide are chosen such that the rate of addition is
between 1 and 20 per glycoside molecule, values according
to the invention preferably being >5, in particular
8 - 25. The reaction to give the sulfosuccinate is
carried out with maleic anhydride and subsequent
sulfonation with sodium sulfite according to processes
known per se (compare German Published Specification
2,700,072).
Reaction is carried out in this case with one mol
of maleic anhydride per mol of hydroxyl group to be
reacted at 60 - 80C until the reaction is complete. The
maleic acid hemiester is then added to an agueous sodium
sulfite solution (1 equivalent of sulfite per equivalent
of hemiester) and sulfonated at 60 - 80C until the
sulfite has completely reacted. The aqueous product is
then adjusted to neutral pH.
While commercial sulfosuccinates can only be
dissolved in water in concentrations up to about 40 % by
weight, the compounds according to the invention
surprisingly have the advantage that they can be prepared
in concentrations of 50 % by weight and higher as clear,
low-viscosity solutions.
These compounds, which can be additionally used
on their own or in a mixture, can be employed in
concentrations of 5 - 20, preferably of 6 - 12 % by
weight, relative to the total mixture.


2 ~ 8 2


The number of anionic groups in the molecule is
affected by the manner in which the glycoside molecules
are linked to one another. If the glycoside rings are
linked to one another in the 1,4- or 1,3-position, it is
simpler for steric reason~ to substitute all the hydroxyl
groups than if the linkage is effected in the 1,6- or
1,2-position.
Although theoretically 2n+1 anionic groups can be
introduced into the glycoside ester, 2n to n groups are
preferred according to the invention.
The mixtures according to the invention are in
general aqueous compositions or aqueous alcoholic
solutions, creams, emulsions or gels and can still
contain the auxiliaries and additives customary in each
case for adaptation to the intended application and
which, apart from in aqueous cleaning agents, such as
mild washing-up liquids used by hand, are in particular
additionally used for the production of cosmetic
preparations in the area of hair- and body-cleaning, that
i8 to say for shower baths, foam baths, shampoos, liquid
soaps, baby care agents and baby detergents.
These are foam stabilizers such as
polysaccharides, carboxyvinyl polymers, polyvinyl-
pyrrolidones, fatty acid partial glyceride polyglycol
ethers, protein-fatty acid condensates; pearl luster and
clouding agents such as fatty alcohols, ethylene glycol
distearates, monoesters of polyhydric alcohols with
higher fatty acid~, polystyrene emulsions; complexing




-
''

2 ~ 2

-- 10 --

agents or sequestering agents such as salts of ethylene-
diaminetetraacetic acid; preservatives such as sorbic
acid, citric acid, ascorbic acid, chlorhexidine, 8-hy-
droxyquinoline and its salts, benzalkonium chloride,
dimethylalkylbenzylammonium chloride and small amounts of
fragrances, colorants, skin cosmetic active substances,
vegetable extracts and buffer substances.
Thickeners additionally used according to B) can
according to the invention be commercial fatty acid
partial glyceride polyglycol ethers such as REWODERNP LI
420, REWODERNP LI 48 (trademark of REWO Chemische Werke
GmbH, Steinau an der Strafle3 in amounts from 1 to 10,
preferably from 2 to 4 % by weight, relative to the total
mixture.
Suitable electrolyte salts are all alkali metal,
alkaline earth metal and ammonium salts which are soluble
at 20C in amounts of at least 1 % by weight. Those
preferred are sodium chloride, magnesium chloride and
ammonium chloride, which can be additionally employed in
amounts up to about 10 % by weight, preferably 1 - 5 % by
weight, relative to the total formulation.
The content of wash-active substance (B-WAS)
given in the following examples is titrated by the
customary two-phase titration with benzalkonium chloride
against Methylene Blue as indicator (cf. S. R. Epton,
Nature (London), 160, 1967, p. 795).
~ he hydrolysis number is a measure of the free
and bound acids contained in fats and technical fatty


. . 20~82


acids. It gives the number of milligrams of potassium
hydroxide which axe necessa~y to hydrolyze 1 gram of
substance or technical fatty acids (mg of ROH/g). The
values are determined by the standard methods of the
German Society for Fat Chemistry (DGF): DGF C-V3.
The hydroxyl value is used to determine the
content of hydroxyl groups and gives the number of
milligrams of potassium hydroxide which are necessary to
neutralize the acetic acid consumed by 1 gram of
substance during the acetylation (mg of KOH/g). The
values are determined by the DGF standard method DGF
C-V17A.
The solids content is determined by drying to
constant weight at 105C.



Pre~aration of the compounds accordina to the invention



Exam~le 1
Preparation of butvlalucoside coconut fatty acid ester
8 g of R2CO3 are added to 826 g (3.5 mol) of
n-butyl~lucoside and the reaction mixture is heated to
120C. 750 g of coconut methyl ester are added dropwise
to the reaction mixture at 50 mbar over the course of 2
h and it is then reacted for 4 h at 120C and 30 mbar.
The resulting methanol is immediately removed by
distillation during the course of this. A yellow, highly

viscous material having the following analytical data
results:




.

2~6~482

- 12 -


Hydrolysis value 110 mg of KO~/g
Hydroxyl value 430 mg of KOH/g



Example 2
Preparation of the PolyethYlene oxide ether
463 g of (1.05 mol) of butylglucoside ester from
Example 1 are treated with 2.3 g of KOH and treated in
portions with 464 g (10.5 mol) of ethylene oxide at 120C
in an autoclave so that the pressure is at most 5 bar. A
highly viscous yellow material having the following
analytical values results:
Hydrolysis value 54 mg of KOH/g
Hydroxyl value 223 mg of KOH/g



Exam~le 3
Pre~aration of the sulfosuccinate
258 g (0.3 mol) of butylglucoside ester
ethoxylate from Example 2 are stirred with 57.6 g
(0.6 mol) of maleic anhydride at 70C for 2 h. The maleic
acid hemiester is then added to a solution of 350 g of
water at 60C containing 74.1 g (0.6 mol) of Na2SO3 and
stirred at this temperature until the SOz content of the
solution is <0.01 %. A clear solution having a 48.3 ~
solids content and 43.5 ~ Benzavlon wash-active substance

(B-WAS) results.
The following examples were carried out following
Examples 1 - 3.


2~482

- 13 -


ExamPle 4
258 g (0.3 mol) of butylglucoside ester
ethoxylate from Example 2 are reacted as described in
Example 3 with 29 g (0.3 mol) of maleic anhydride and
then sulfonated in a solution of 300 g of water
containing 37 g (0.3 mol) of Na2S03. The solution has a
solids content of 49 % and a B-WAS of 41 %.



Example 5
258 g (0.3 mol) of butylglucoside ester
ethoxylate from Example 2 are reacted as described in
Example 3 with 87 g (0.9 mol) of maleic anhydride and
then sulfonated with a solution of 400 g of water
containing 111 g (0.9 mol) of Na2S03. The solution has a
solids content of 47 % and a B-WAS of 43 %.



Example 6
200 g (0.3 g mol) of butylglucoside ester
ethoxylate (as example 2, but ~Y = 5) are reacted with
59 g (0.6 mol) of maleic anhydride at 80C. A~ described
in Example 1, the hemiester is then sulfonated in a
solution of 330 g of water and 77 g (0.61 mol) of Na2S03.
The sulfosuccinate has 49 % solids and a B-WAS of 41 %.




Example 7
200 g (0.3 mol) of the butylglucoside ester
ethoxylate as described in Example 6 are reacted with
88.5 g (0.9 mol) of maleic anhydride at 80C. Analogously


2~S~g2

- 14 -


to Example 3, the sulfonation is carried out in 400 g of
water and 116 g of Na2SO3. The sulfosuccinate has 50 %
solids and a B-WAS of 44 %.



Example 8
200 g (0.3 mol) of butylglucoside ester
ethoxylate as in Example 6 are reacted with 29.5 g
(0.3 mol) of maleic anhydride at 75C. Analogously to
Example 3, sulfonation is carried out in 270 g of water
containing 38 g (0.3 mol) of Na2SO3. The sulfosuccinate
has 48.2 ~ solids together with 28.1 % B-WAS.



Example 9
220 g (0.5 mol) of butylglucoside ester from
Example 1 are reacted analogously to Example 3 with 49 g
(0.5 mol) of maleic anhydride and then sulfonated in
500 g of water containing 63 g (0.5 mol) of Na2SO3. The
sulfosuccinate has 38.3 ~ solids and a B-WAS of 23.2 %.



Example 10
238 g (1 mol) of butylglucoside are treated with
0.5 g of potassium hydroxide and treated in portions with

440 g (10 mol) of ethylene oxide at 140C in an autoclave
80 that the maximum pressure does not exceed 5 bar. A
viscous~ yellow product having a hydroxyl value of 360
results.


2~4~

-- 15 --

Example 11
678 g (1 mol) of the product from Example 10 are
treated with 3 g of K2CO3 and heated to 120C under an N2
atmosphere. Under a vacuum of 100 mbar, 210 g (0.95 mol)
of coconut methyl ester are added dropwise to the
reaction solution over the course of about 2 h and the
mixture is then reacted for a further 4 h at 120C. The
resulting methanol is continuously removed from the
system. A pale-yellow, viscous material having the
following analytical values re~ults:
Hydrolysis value 60
Hydroxyl value 240



Example 12
890 g (l mol) of butylglucoside ethoxylate ester
from Example 11 are reacted as described in Example 3
with 98 g (1 mol) of maleic anhydride and then sulfonated
with a solution of 1100 g of water and 126 g of Na2SO3. A
pale solution having a solids content of 49 % and a B-WAS
of 31 % results.


2 ~ 8 2
-- 16 --

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- 2~482
- 17 -


All recipes are given in percent by weight
calculated relative to solids.



Statement of the surfactants employed according to the
Cosmetic, Toiletry and Fragrance Association (CTFA)
standards:
1) Disodium laureth sulfosuccinate
2) Sodium laureth sulfate
3) Cocoamidopropyl betaine
4) PEG-80 glyceryl tallowate
5) Glyceryl stearate
6) PEG-200 glyceryl tallowate mod.
7) Disodium cocoamphodiacetate



Basic reciPe~ hair shamPoo
Example 4 or 12 2 - 6 parts by weight
REWOPOL~ NL 3-28 6 - 15 "
REWODERM~ LI S 756) 1 - 3 "
demin. water to 100



Basic reciPe, babv shampoo or shampoo for sensitive skin
Example 4 or 12 3 - 8 parts by weight
REWOTERIC AM 2 C NM7) 2 - 10 "

REWOTERIC AM B 13 H3) 4 - 8 "
REWODERM? LI 48-504) 1 - 4 "
demin. water to 100

-- 2 ~ 8 2

- 18 -

Basic recipe cream
Example 4 or 12 1 - 5 parts by weight
Glycerol monodistearate 2 - lO "
Cetyl alcohol l - 4 "
Paraffin oil 3.5E 4 - 12 "
Glycerol 1 - 5 "
demin. water to 100
Preservative as required

Basic recipe shower bath
Example 4 or 12 2 - 10 parts by weight
REWOTERIC AM B 13 2 - 8 "
REWOPOL NL 3-28 5 - 15 "
REWODERN~ LI 48-50 1 - 4 "
demin. water to lOO

Basic reci~e washina-up lia,uid
Example 12 l - 5parts by weight
REWOPOL NL 3-28 1 - 30 "
REWOTERIC AM CAS 1 - 5 "
REWOPOL LA 6 1 - 10 "
demin. water to lOO

Application check
Shower bath
The glyco~ide derivatives developed have been
asse~sed in the test recipe by a test panel of 20 persons
(female and male) with respect to

2~6~
-- 19 --

- foaming power, foam structure
- feeling of the wet skin
- feeling of the dried skin
for skin compatibility (zein ~alues) compare:
Z. Gotte "Hautvertraglichkeit von Tensiden, gemessen am
Loseverm~genfur Zein~(skin compatibility of surfactants,
measured by dissolving power for zein) Chem. Phys. Appl.
Surface Active Subst. Proc. Int. Congr. 4 (1964~ 83 - 90.
Assessment scheme: ~ 200 mg of N/100 ml = non-irritating
200 - 400 mg of ~100 ml = slightly
irritating
> 400 mg of N/100 ml = irritating



Plate washina test
1. Princi~le
The number of artificially soiled plates which
can be cleaned in a washing-up liquid solution until the
liquor is exhausted is determined.



2. Production of the test soilina
2.0 parts by weight of technical oleic acid, 49.9
parts by weight of wheatmeal flour and 0.1 part by weight
of the dye Sudan Red are successively stirred into a melt
of 48.0 parts by weight of lard at S0C and homogenized.




3. Coatina the Plate
The plates are first washed, rinsed with clear
water and additionally rinsed with isopropanol. 2 g of




.

~ - 20~82
- 20 -


the test soiling at 40C are then uniformly distributed
on each dried plate on the inner surface using a brush
and then stored for 24 h at 20C and 65 ~ relative
atmospheric humidity.



4. Pre~aration of the washina liauors
Washing liquor A:
8 1 of tap water at 50C having a German hardness
~dH) of 10 and a content of the test substance to be
checked of 0.02 ~ by weight (relative to solids) is
placed in a bowl and stirred for 2 min with a blade
stirrer at 300 rpm in such a way that sufficient foam
results.



Washing liquor Bs
10 1 of cold tap water (20C 10dH) which is
continuously replaced by running fresh water (5 l/min)
are placed in a second bowl.



S. Washina ~rocess
The soiled plates are washed in 6uccession for 30
seconds each under the surface of the washing liquor A
using the washing brush. They are then rinsed by simple

immersion in liquor B. Washing is carried out until
liquor A is exhausted. This is recognized by the
disappearance of the foam, the visually recognizable
remaining of soil particles on the washed plates or the
floating of black or red fat particles on the surface of




~ , '
, ' - ' .
.

2 ~ 8 2

- 21 -


the liquor A.



6 ! Assessment
The number of plates washed perfectly clean is
determined by sub~ective assessment of at least 3
persons. The following are stated:
Number of plates as stated
Concentration of the washing
liquor in g/l 0.02 % solids content
Water hardness in mmol of Ca~/l 10dH
Washing temperature in C 50




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20~82
-- 22 --

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- 206~2
- 24 -


Hair_shampoo
The glycoside derivatives developed have been
assessed in the recipe by 10 volunteers experienced in
application for:
- Combability
- Volume of the hair and hold of the hairstyle



Recipe 1 2 3


Example 4 4.5 _ _
Example 12 _ 4.5 _
REWOPOI~ NL 3-282) 10.5 10.5 15
REWODERM~ LI S 756) 2 2 2
demin. water 83 83 83

pH ad~usted with citric
acid to 6.5 6.5 6.5
Combability 5 6 2

Volume of the hair
Hold of the hairstyle 6 5 3



Assessment of combability:
1 - 3 Difficult to comb through: the hair offers
considerable resistance to the combing process

4 - 7 The hair can be combed through relatively easily,
combing resistance is decrea~ed, adequate for a
conditioning shampoo depending on the hair type
8 - 10 Reserved for the subsequent aftertreatment by so-
called hair-rinse agents


20~82
- 25 -


Assessment of the hair volume and of the hold of the
_airstyle
1 - 3 The hair is dry or dull and lifeless; poor hold
of the hairstyle
4 - 7 The hair is soft and bouffant at the same time
together with a good hold of the hairstyle
8 - 10 The hair i8 soft and smooth, but too loose, as a
result the hairstyle does not hold well.
- The assessment was carried out by a graded point
system, where the abovementioned assessment represents
the arithmetic mean.



Skin cream
Use of aqueous sulfosuccinates based on glycoside
as emulsifiers in 0/W emulsions
HLB value Example 4 about 16
Example 12 about 16
Determination according to W.C. Griffin ("Calculation of
Surface Active Agents by HLB", Journal Soc. Cosm.
Chem. 1, 311 (1949)).




: . ' '

' ' : . :'
.
.

.. '

. . 20~82
-- 26 --



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JJ
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.Y x x ~ eO ~
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:: '

.

2 ~ 8 2
- 27 -


Assessment of the properties on the skin by 10
volunteers; more than 80 % assessed the stable test
recipes 1 and 2
- as easy to spread on the ~kin
- as easily absorbed into the skin
- the skin is smooth and soft, without becoming sticky
and greasy. The comparison recipe No. 4 is not
assessed the same and is furthermore unstable.



Babv shamPoo or hair and bodv shampoo for sensitive skin



Recipe 1 2 3


Example 4 6 _ _
Example 12 _ 6 _
REWOTERIC~ AM 2C NM7) 6 6 6
REWOTERIC~ AM B 133) 4 4 4
REWODERM~ LI 48-504~ 2 2 2
REWOPOL2 NL 3-282) _ _ 6
demin. water to 100 to 100 to 100

pH adjusted with citric
acid to 6.5 6.5 6.5
Zein values, mg of N/100 ml ~70 ~70 about 150


Skin roughness according to slight slight di~tinct
Padberg~) rough- rough- rough-
ening ening ening



The recipe shown is a "non-irritating" washing
solution only "slightly roughening" the skin. The
assessment "slightly roughening" is the lowest which can


--- 2 ~ 8 2
- 28 -

be obtained with surfactants by the method shown.
Testing of skin compatibility according to Padberg,
J. Soc. Cosm. Chem. 20, 719 - 728 (1969)

Assessment of skin roughness according to Padberg:
Grade 1 very slight roughening - does not differ from the
blank area
Grade 2 slight roughening - % Padberg below 50
Grade 3 distinct roughening - % Padberg over 50
Grade 4 heavy roughening - does not differ significantly
from the sodium lauryl sulfate area
(comparison substance)




' -
~' ' .

20~82
- 29 -

Test recipe: Skin-compatible washina-up aaents for
manual use

Recipe 1 2 3 4
.



Example 12 _ 3 1.5 _
REWOPOI~ NL 3-28 7) 18 18 18 18
REWOTERIC~ AM CAS 3) 1 . 5 _ 1.5 _
REWOPOL LA 6 4) 1 . 5 _ _ 3
Water to 100 to 100 to 100 to 100


Plate washing test
Number of plates 12 20 18 12


Zein values
(skin compat-
ibillty) 220 lg5 220 250
.
'~

Foam height (mm) 195/185 190/180 195/190 190/180
+ 0.S ml of
Olive oil 190/180 190/180 195/185 190/180
+ 1.0 ml of
Olive oil 190/185 190/180 190/180 190/180



:'


. .
- ... ~.

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(22) Filed 1992-03-31
(41) Open to Public Inspection 1992-10-05
Dead Application 1997-04-01

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1992-03-31
Registration of a document - section 124 $0.00 1992-10-26
Maintenance Fee - Application - New Act 2 1994-03-31 $100.00 1994-02-18
Maintenance Fee - Application - New Act 3 1995-03-31 $100.00 1995-02-16
Registration of a document - section 124 $0.00 1995-10-05
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
WITCO SURFACTANTS G.M.B.H.
Past Owners on Record
HINTZ, MATHIAS
KOHLE, HANS-JURGEN
MOLLER, CHRISTL
REWO CHEMISCHE WERKE G.M.B.H.
SALOMON, THOMAS
WEIGAND, JOACHIM
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) 
Drawings 1992-10-05 1 7
Claims 1992-10-05 5 120
Abstract 1992-10-05 2 27
Cover Page 1992-10-05 1 25
Description 1992-10-05 29 758
Fees 1995-02-16 1 61
Fees 1994-02-18 1 42