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Patent 2267377 Summary

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(12) Patent Application: (11) CA 2267377
(54) English Title: CAST MELT BAR COMPOSITIONS COMPRISING HIGH LEVELS OF LOW MOLECULAR WEIGHT POLYALKYLENE GLYCOLS
(54) French Title: COMPOSITIONS DE PAINS DE SAVON COULES, A FORTE TENEUR EN POLYALKYLENE GLYCOLS A FAIBLE POIDS MOLECULAIRE
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11D 17/00 (2006.01)
  • C11D 1/83 (2006.01)
  • C11D 1/94 (2006.01)
  • C11D 3/22 (2006.01)
  • C11D 3/37 (2006.01)
  • C11D 10/04 (2006.01)
(72) Inventors :
  • HE, MENGTAO (United States of America)
  • DALTON, JAMES JOSEPH (United States of America)
  • DANIELS, KENNARD (United States of America)
  • SHAFER, GEORGIA LYNN (United States of America)
  • MASSARO, MICHAEL (United States of America)
(73) Owners :
  • UNILEVER PLC
(71) Applicants :
  • UNILEVER PLC (United Kingdom)
(74) Agent: SMART & BIGGAR LP
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1997-10-01
(87) Open to Public Inspection: 1998-04-23
Examination requested: 2000-01-11
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/EP1997/005576
(87) International Publication Number: WO 1998016620
(85) National Entry: 1999-03-31

(30) Application Priority Data:
Application No. Country/Territory Date
08/733035 (United States of America) 1996-10-16

Abstracts

English Abstract


The present invention relates to skin cleansing bar composition in which
polyalkylene glycols of very specific molecular weights are used to define
compositions which are mild, foam well and provide consumer-desired sensory
profiles. A significant amount of these specific PEGs must be incorporated
into the bar to deliver these desired effects. To properly process such a bar
composition, the cast-melt method is the preferred technique.


French Abstract

La présente invention concerne une composition de pain de savon destiné au nettoyage de la peau dans laquelle des polyalkylène glycols de poids moléculaire très spécifique sont utilisés pour définir des compositions douces, qui moussent bien et présentent des profils sensoriels voulus par les consommateurs. On doit incorporer au pain de savon une quantité substantielle de ces polyéthylène glycols spécifiques pour obtenir ces effets voulus. Le procédé approprié de fabrication d'une telle composition de pain de savon consiste en une technique de moulage par coulée.

Claims

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


-28-
CLAIMS
1. A skin cleansing bar composition comprising:
(a) 2% to 35% by wt. synthetic, non-soap anionic
surfactant;
(b) 0 to 20% by wt. amphoteric, zwitterionic, or
nonionic surfactant or mixtures thereof;
(c) 10% to 70% by wt. of polyalkylene glycols having
molecular weight of greater than 300 to about
l500; weight ratio of (c) to (a) being greater
than 1:1;
(d) greater than about 1% to 20% by wt. of gelling
agents;
(e) 2% to less than 10% by wt. water.
2. A composition according to claim 1(d), in which the
gelling agents are selected from the group consisting of C8
to C25 neutralized carboxylic acids (soap), paraffin waxes,
polyethylene waxes, glyceryl stearate, petrolatum, greases,
jellies, fumed silica, alumino silicates, urea, clay and
mixtures thereof;
3. A composition according to claim 1, wherein 0% to 35%
by weight of solid structurants and fillers selected from
the group consisting of C8 to C25 fatty acids, C8 to C20
alkanols, water soluble starches (i.e., maltodextrin),
polyalkylene glycol having molecular weight between 2500 and
10000, and mixtures thereof are included;

-29-
4. A composition according to claim 1(c), in which the
weight ratio of the polyalkylene glycol (1(c)) to the
anionic surfactant (1(a)) is greater than 2:1;
5. A composition according to claim 1(a), wherein the
synthetic, non-soap anionic surfactant comprises 10% to 30%
by wt. of the total composition;
6. A composition according to claim 1(b), wherein the
amphoteric and zwitterionic surfactants comprise 2% to 15%
by wt. of the total composition;
7. A composition according to claim 1(c), wherein the low
molecular weight polyalkylene glycol has the following
structure
<IMG>
wherein R1 = H, C1 to C4 alkyl;
R2 = H , CH3 ; and
n is greater than 6 and less than 35;
8. A composition according to claim 2, wherein the
neutralized fatty acid (soap) is a straight chain,
saturated, C12-C22 neutralized monocarboxylic acid;

-30-
9. A composition according to claim 3, wherein the
structurant is C8 to C25 carboxylic fatty acid, and the fatty
acid comprises 5% to 25% by weight of the total composition;
10. A composition according to claim 3, wherein the
structurant is fatty acid, and fatty acid is a straight
chain, saturated C12 to C22 monocarboxylic acid;
11. A composition according to claim 3, wherein the alkanol
is cetyl alcohol;
12. A composition according to claim 1(c), wherein the
polyalkylene glycols have molecular weight of greater than
350 to about 1500 Dalton.

Description

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


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CAST MELT BAR COMPOSITIONS COMPRISING HIGH
LEVELS OF LOW MOLECULAR WEIGHT POLYALKYLENE GLYCOLS
FIELD OF THE INVENTION
The present invention relates to skin cleansing bar
compositions preferably formed by cast melt method. These
bars are extremely mild, foam well and provide consumer-
desired sensory properties.
BACKGROUND
Personal washing bars are constantly moving toward
milder formulations that ultimately will provide some
enhanced skin care, for example, minimizing levels of skin
irritation and enhancing moisturization. It is desirable to
have a bar composition that carries a significant amount of
emollient oily liquid that provides positive sensory cues to
many consumers. To properly process such a bar composition,
cast-melt is the preferred technique.
It is a challenge to find an economical bulk chemical
which can function as a bar filler/binder that enhances skin
mildness or moisturization, promotes bar lather performance
and facilitates bar processing. For example, solid
polyalkylene glycols (e. g., polyethylene glycols (PEG)
having molecular weight above 2000) are effective bar
structurants and they do not defoam. However, in comparison

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to a PEG having a lower molecular weight, they provide much
less oily skin feel which signals moisturization to many
consumers, and they are less readily miscible with long
chain fatty acid soaps that are used as gelling agents in
the subject invention. Solid fatty acids, on the other hand,
can effectively structure bar but tend to defoam. Paraffin
waxes defoam if included in a bar at relatively high levels
(i.e., greater than 25o wt. total composition), especially
in the presence of hydrophobic emollient oils.
In the subject invention, applicants have formulated
relatively high levels of low molecular weight polyalkylene
glycols (e. g., polyethylene glycol having molecular weight
of 300 to 1500) in a synthetic detergent bar using the cast
melt technology. In-vivo and in-vitro data showed that,
only at high levels of addition (polyethylene glycol to
anionic weight ratio at 1:1 and above) do these low MW PEGS
significantly mitigate the irritation potential of commonly
used anionic surfactants. Unlike solid PEGS with molecular
weight greater than 2000, the low molecular weight PEGS are
more readily miscible with long chain fatty acid soaps that
are the gelling agents of this invention, and therefore are
a significant component of the immobilized liquid fraction
of these bars. It is this liquid fraction that readily
dissolves upon use providing the benefits of enhanced skin
feel, mildness and lather. As an additional benefit, the
low molecular weight PEGS enhance desired lather properties
to a skin cleanser.

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Thus using high levels of these relatively low
molecular weight materials, applicants were able to obtain
bars which simultaneously (1) provided desired user and
processing properties (2) lathered well and (3) were less
irritating.
The use of polyalkylene glycol (e. g., polyethylene
glycol) in. personal washing bar compositions is not itself
new.
U.S. Patent No. 3,312,627, to D. Hooker, for example,
teaches a bar composition containing 30-70% polyethylene
glycol (PEG) as bar structurant for a nonionic formulation
basically free of anionic detergents. The PEG used in this
invention has a molecular weight above 4000 Dalton, which is
significantly higher than the MW claimed for the PEGS
applied in the subject invention (<1500). In contrast to
the subject invention, the referred patent used
significantly higher level of high MW PEG in total bar
composition. Further, the PEG/anionic surfactant ratio is
not important in this patent since it refers to a primarily
nonionic formulation.
World Patent Application No. 93/07245 to F. Moran, B.
0'Briain and D. Moran (assigned to NEPIiIN) teaches a shampoo
bar composition containing 12-20% synthetic detergents and
70-80o PEGS with molecular weight between 5000 and 10,000.
An embodiment of the invention includes a softening PEG with
molecular weight between 100 and 800 (preferably 1-8% wt.

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- 4 -
total composition). In contrast to the subject invention,
the referred patent application used a significant level
(70-80o) of high MW PEGS in total bar composition. The
referred patent used significantly less amount of low MW PEG
than used in the subject invention.
In applicant's copending application No. W094/21778,
corresponding to U.S. Serial No. 08/594,363, which in turn
is a Continuation of U.S. Serial No. 08/213,287, entitled
"Synthetic Detergent Bar and Manufacture Thereof", to J.
' Chambers et al., there is taught a bar containing 10-600
synthetic surfactants and 10-60o PEG as structurant. The
PEG used has a range of melting temperatures between 40~C and
l00~C, and a range of molecular weight between 1500 and
10,000. This molecular weight makes PEG a solid at room
temperature. The PEG molecular weight used is above that
claimed (<1500) by the subject invention. Also the referred
patent application does not teach PEG/anionic ratio of at
least 1:1 that is relevant to the mildness enhancement, a
criticality of the subject invention.
U.S. Patent No. 5,520,840 to M. Massaro et al. teaches
a skin cleansing bar composition containing 10-60~ of
synthetic surfactant, 10-60~ water soluble structurant
(e. g., PEG) with having a range of melting points between
40~C and 100~C, and 1-25~ water soluble starch such as
maltodextrin. The molecular weight of the PEGS used (>
1500) is above that claimed for the subject invention. Also
the referred patent application does not teach a PEG/anionic
ratio of at ~Ieast 1:1 that is relevant to the mildness
enhancement, a criticality of the subject invention.
HwiENDED SHEET

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_ 5 _
U.S. Patent No. 2,287,484 to Lundberg teaches a bar
made by a closed die molding technique which comprises 35-
700 of anionic synthetic surfactant and 22-50~ fatty acid.
The bar also may contain up to loo ethylene and di-ethylene
glycols as additives. As found by the subject invention,
the ethylene and di-ethylene glycols are not as effective as
low MW PEGS (MW above 300) in reducing the skin irritation
of anionic surfactants. Also the referred patent does not
teach a PEG/anionic surfactant weight ratio of at least 1:1
that is relevant to the mildness enhancement, a criticality
of the subject invention.
Applicants' copending application V7097/47722,
corresponding to US application No. 08/662,394, filed June
12, 1996 teaches a mild bar composition containing 10-600
synthetic detergents, 10-50o high molecular weight PEG with
melting point above 40~C and 0.1 to 10o low molecular weight
PEG (melting point below 40~C) as processing aid. The
application claims the use of relatively low levels of low
MW PEG as a lubricant to aid the extrusion process. This is
significantly different from the art of the subject
invention, which formulated relatively high levels of low MW
PEG (e.g., >10o wt. total composition) into a bar as a
moisturizer. Also the referred patent application did not
specify the PEG/anionic surfactant weight ratio, which is a
criticality of the subject invention to achieve superior
skin mildness.
~,,1~ ~,~~Fn y-;;=y.?

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U.S. Patent Nos. 5,262,079 and S,227,086 to M. Kacher,
J. Taneri, D. Quiram, D. Schmidt and M. Evans teach a framed
cleansing bar composition containing 5-500 of a mixture of
free and neutralized monocarboxylic acid, 15-65o synthetic
anionic and nonionic bar firmness aid and 15-S5o water. The
bar firmness aid consists of 5-50o synthetic surfactants and
0-40o polyethylene glycol or polypropylene glycol with MW
ranging from approximately 44 to 10,000 Dalton. The
referred patents do not teach or suggest use of PEGS with MW
between 400 and 1500 with specific PEG/anionic surfactant
weight ratios to achieve both enhanced cast-melt
processibility and mildness enhancement. Further, to obtain
the desired bar user properties (i.e., mush and hardness)
the applicants of the subject invention include only 2-100
wt. water in the bar compositions claimed, which is
significantly below the 15-55o water claimed by the referred
patents.
Finally, applicants have concurrently filed W098/16619,
corresponding to US serial no. 08/733 036, which is an
application entitled "Pourable Cast Melt Bar Compositions
Comprising Low Levels of Water and Minimum Ratios of Polyol
to Water". The subject invention is made by the same cast
melt methodology. However, the related application is not
directed to specific compositions wherein high levels of
polyalkylene glycol with molecular weight between 400 and
1,500 are used and ratio of polyalkylene glycol to anionic
surfactant is at least 1:1.
a~lE~IDED SNF~

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BRIEF SUMMARY OF THE INVENTION
The present invention relates to bar compositions in
which alkylene glycols (e. g., polyethylene glycols) of very
specific molecular weight range (high enough molecular
weight to mitigate harshness effect of anionic, but low
enough MW to provide the desired sensory profile and
facilitate the cast-melt processing) are used and ratio of
alkylene glycol to anionic is maintained at least 1:1 and
higher. Such compositions are mild, foam well and provide
consumer desired sensory profiles.
More specifically, the invention comprises:
(1) 2 to 35%, preferably 10 to 30% by wt. of the total
composition of synthetic anionic surfactant;
(2) 0 to 20% by wt. of the total composition of
surfactant selected from the group consisting of
amphoteric, zwitterionic nonionic and mixtures
thereof; preferably amphoteric and zwitterionic
surfactants comprise 2 to 15% by wt. of the total
composition;
(3) 10% by 70% by wt. of the total of the composition
of a polyalkylene glycol or mixture of
polyalkylene glycol compounds having MW greater
than 300 to about 1500 Dalton;

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the weight ratio of the polyalkylene glycol to the
anionic surfactant being at least 1:1, preferably 2:1
and greater;
(4) about 0% to 35% by wt. of the total composition
of solid structuring aids and fillers selected
from the group consisting of (i) polyalkylene
glycols having MW of 2500 to 10,000 and MP of
about 55~ to 65~ C; (ii) preferably straight chain,
preferably saturated C8 to C24 free fatty acids;
(iii) preferably straight chain, preferably
saturated C8 to CZO alkanols; (iv) water soluble
starches (e. g., maltodextrin);
(5) about 1% to 20% by wt. of the total composition of
gelling agent; and
(6) about 2% to 10% by wt. of the total composition of
water.
BRIEF DESCRIPTION OF DRAWINGS
Figure 1 is a graph showing that polyethylene glycol
with molecular weight of 400 and above significantly reduce
the amount of zero dissolved by acyl isethionate (i.e., is
less harsh) when weight ratio of PEG to isethionate is above
1:1, preferably above 2:1.
Figure 2 shows that, at molecular weight below 400,
PEGS or other water soluble nonionic monomer (e. g. ethylene

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glycol, propylene glycol) do not reduce the amount of zero
dissolved by isethionate.
Figure 3 shows that at molecular weight below 400, PEGS
or other water soluble nonionic monomer do not reduce the
amount of zero dissolved by sodium lauryl ether sulphate.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to compositions in which
alkylene glycols within a very specific molecular weight
range (high enough to mitigate harshness effect of anionic
surfactant, but low enough MW to provide consumer-desired
sensory profile and facilitate the cast-melt processing) are
used at a minimum ratio of alkylene glycol to anionic to
provide compositions which are (1) mild, (2) maintain good
foam profile and (3) provide both consumer-desired sensory
profiles (i.e., due to lower molecular weight) and
processing benefits.
More specifically, the composition comprises:
(1) 2 to 35%, preferably 10 to 30% by wt. of the
total composition of synthetic anionic surfactant;
(2) 0 to 20% by wt. of the total composition of
surfactant selected from the group consisting of
amphoteric, zwitterionic nonionic and mixtures
thereof; preferably amphoteric and zwitterionic

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surfactants comprise 2 to 15% by wt. total
composition;
(3) 10~s by 70o by wt. of the total composition of a
polyalkylene glycol or mixture of polyalkylene
glycol compounds having MW greater than 300 to
about 1500 Dalton;
the weight ratio of the polyalkylene glycol to the
anionic surfactant being at least 1:1, preferably 2:1
and greater;
(4) about 0% to 35% by wt. of the total composition of
solid structuring aids and fillers selected from
the group consisting of (i) polyalkylene glycols
having MW of 2500 to 10,000 and MP of about 55~ to
65~ C; (ii) preferably straight chain, preferably
saturated Ce to C24 free fatty acids; (iii)
preferably straight chain) preferably saturated Ce
to CZO alkanols; (iv) water soluble starches (e. g.,
maltodextrin);
(5) Further, because the high levels of low MW
polyalkylene glycol are in the form of liquid or
paste, about 1% to 20% by weight of the total
composition of gelling agents, as described more
specifically below, are used to enhance bar integrity;
and

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(6) about 2% to 10% by weight of the total composition
of water .
Synthetic Non Soap Surfactant
The surfactant system of the invention will generally
comprise at least one anionic surfactant as well as an
optional second surfactant which is selected from the group
consisting of amphoteric/zwitterionic surfactant, nonionic
or mixtures thereof. Preferably, the composition comprises
an anionic or anionic surfactant and an
amphoteric/zwitterionic.
The anionic surfactant which may be used may be
aliphatic sulfonates, such as a primary alkane (e. g., CB-C22)
sulfonate, primary alkane (e.g. , Ce-C22) disulfonate, C8-C22
alkene sulfonate, C8-C22 hydroxyalkane sulfonate or alkyl
glyceryl ether sulfonate (AGS); or aromatic sulfonates such
as alkyl benzene sulfonate.
The anionic may also be an alkyl sulfate (e.g., C12-C1g
alkyl sulfate) or alkyl ether sulfate (including alkyl
glyceryl ether sulfates). Among the alkyl ether sulfates
are those having the formula:
RO ( CH2CH20) nS03M
wherein R is an alkyl or alkenyl having 8 to 18
carbons, preferably 12 to 18 carbons, n has an average value

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of greater than 1.0, preferably greater than 3; and M is a
solubilizing cation such as sodium, potassium, ammonium or
substituted ammonium. Ammonium and sodium lauryl ether
sulfates are preferred.
The anionic may also be alkyl sulfosuccinates
(including mono and dialkyl, e.g., C6-C22 sulfosuccinates);
alkyl and acyl taurates, alkyl and acyl sarcosinates,
sulfoacetates, C8-C22 alkyl phosphates and phosphates, alkyl
phosphate esters and alkoxyl alkyl phosphate esters, acyl
lactates, Ca-C22 monoalkyl succinates and maleates,
sulphoacetates, alkyl glucosides and acyl isethionates.
Sulfosuccinates may be monoalkyl sulfosuccinates having
the formula:
R102CCH2CH (S03M) C02M; and
amide-MEA sulfosuccinates of the formula
R1CONHCH2CH202CCH2CH (S03M) C02M
wherein Rl ranges from CB-C22 alkyl and M is a
solubilizing cation.
Sarcosinates are generally indicated by the formula
RCON(CH3) CF~2COZM, wherein R ranges from CB-C2o alkyl and M is
a solubilizing cation.
Taurates are generally identified by formula

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RzCONR3CH2CHzS03M
wherein RZ ranges from Ce-C2o alkyl, R3 ranges from C1-C4
alkyl and M is a solubilizing cation.
Particularly preferred are the CB-C18 acyl isethionates.
These esters are prepared by reaction between alkali metal
isethionate with mixed aliphatic fatty acids having from 6
to 18 carbon atoms and an iodine value of less than 20. At
least 75% by weight of the mixed fatty acids have from 12 to
18 carbon atoms and up to 25% by weight have from 6 to 10
carbon atoms.
Acyl isethionates, when present, will generally range
from about 10% to about 35% by weight of the total bar
composition. Preferably, this component is present from
about 10% to about 30% by weight.
The acyl isethionate may be an alkoxylated isethionate
such as is described in Ilardi et al., U.S. Patent No.
5,393,466, hereby incorporated by reference. This compound
has the general formula
O X Y
II ! I
R-C-O-CH-CHZ- {OCH-CHz),n-S03M+
wherein R is an alkyl group having 8 to 18 carbons, m is an
integer from 1 to 4, X and Y are hydrogen or an alkyl group

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having 1 to 4 carbons and M+ is a monovalent cation such as,
for example, sodium, potassium or ammonium.
In general the anionic component will comprise from
about 2 to 35% by weight of the bar composition, preferably
to 30% by weight.
Amphoteric detergents which may be used in this
invention include at least one acid group. This may be a
10 carboxylic or a sulphonic acid group. They include
quaternary nitrogen and therefore are quaternary amido
acids. They should generally include an alkyl or alkenyl
group of 7 to 18 carbon atoms. They will usually comply
with an overall structural formula:
O RZ
I
R1 - [-C-NH (CH2)n-Jm-N+-X-Y
(
2 0 R3
where R1 is alkyl or alkenyl of 7 to 18 carbon atoms;
RZ and R3 are each independently alkyl, hydroxyalkyl or
carboxyalkyl of 1 to 3 carbon atoms;
n is 2 to 4 ;
m is 0 to 1;
x is alkylene of 1 to 3 carbon atoms optionally
substituted with hydroxyl, and

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y is -CO2 - or -S03-
Suitable amphoteric detergents within the above general
formula include simple betaines of formula:
R2
I
R1-N+ - CHz C02 _
R3
and amido betaines of formula:
Rz
I
Rl - CONH ( CH2 ) m-N+- CH2 CO2 _
I
R3
where m is 2 or 3.
In both formulae R1 is alkyl or alkenyl of 7 to 18
carbons; and R2 and R3 are independently alkyl, hydroxyalkyl
or carboxylalkyl of 1 to 3 carbons. R1 may in particular be
a mixture of C12 and C14 alkyl groups derived f rom coconut so
that at least half, preferably at least three quarters of
the groups R1 have 10 to 14 carbon atoms. R2 and R3 are
preferably methyl.
A further possibility is that the amphoteric detergent
is a sulphobetaine of formula

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Rz
I
R1-N+- (CHz) 3SO3_
I
R3
or
R2
I
R1 -CONH (CH2) m-N+) - (CHZ) 3S03_
I
R3
where m is 2 or 3, or variants of these in which -
(CH2) 3503_ is replaced by
OH
I _
2 0 - CHZ CHCHZ S03
In these formulae Rl, RZ and R3 are as discussed for the
amido betaine.
Amphoteric, if present, generally comprises 2% to 15%
by weight of the bar composition.
Other surfactants (i.e., nonionics, cationics) may also
be optionally used although these generally would not
comprise more than .O1 to 10% by wt. of the bar composition.

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Nonionic surfactants include in particular the reaction
products of compounds having a hydrophobic group and a
reactive hydrogen atom, for example, aliphatic alcohols,
acids, amides or alkyl phenols with alkylene oxides,
especially ethylene oxide either alone or with propylene
oxide. Specific nonionic detergent compounds are alkyl (C6-
C22) phenols-ethylene oxide condensates, the condensation
products of aliphatic (C8-C18) primary or secondary linear or
branched alcohols with ethylene oxide, and products made by
condensation of ethylene oxide with the reaction products of
propylene oxide and ethylenediamine. Other so-called
nonionic detergent compounds include long chain tertiary
amine oxides, long chain tertiary phosphine oxides and
dialkyl sulphoxides.
I5
The nonionic may also be a sugar amide, such as a
polysaccharide amide. Specifically, the surfactant may be
one of the lactobionamides described in U.S. Patent No.
5,3S9,279 to Au et al. which is hereby incorporated by
reference and polyhydroxyamides such as described in U.S.
Patent No. 5,312,954 to Letton et al., hereby incorporated
into the subject application by reference.
Examples of cationic detergents are the quaternary
ammonium compounds such as alkyldimethylammonium
halogenides.
Other surfactants which may be used are described in
U.S. Patent No. 3,723,325 to Parran Jr. and ~~Surface Active

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Agents and Detergents" (Volume I & II) by Schwartz, Perry &
Berch, both of which are also incorporated into the subject
application by reference.
Polyalkvl ene G1 ycol
A second required component of the invention is
polyalkylene glycol or mixture of polyalkylene glycols
wherein the polyalkylene glycol is, for example, a
polyethylene or polypropylene glycol. The polyalkylene
glycols must have a MW of between greater than 300,
preferably greater than about 350 and 1500 Dalton.
This MW range is important because at MW below the
minimum 300 range, the PEG in bar does not significantly
reduce the skin irritation potential caused by anionic
surfactants (see Example 2, Figure 2 and 3); and at MW above
1500, the PEG molecule is not as readily miscible with long
chain fatty acid soaps, which are used as gelling agents.
Also at MW above 1500, the PEG does not provide as much oily
skin feel as a PEG with a lower molecular weight.
It is another important aspect of the invention that
the weight ratio of alkylene glycol to anionic is at least
1:1 and preferably 2:1 and greater. Again, at a weight
ratio below 1:1, the mildness is not readily felt (see
Example 1, Figure 1).

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_ 19 _
Generally, this compound or mixture of compounds will
comprise 10% to 70% by wt. of the bar compositions.
Gelling Agent
A gelling agent is required in the compositions of the
invention. While not wishing to be bound by theory, such
component is believed required because the higher levels of
low MW polyalkylene glycol required by the invention are in
the form of liquid or paste. The gelling agent is believed
needed to enhance bar integrity.
Examples of gelling agents include, but are not limited
to:
(i) neutralized CB to Czs carboxylic acid (soap),
preferably neutralized C8 to C25 monocarboxylic
acid (straight chain, saturated soap);
(ii) paraffin waxes, polyethylene waxes) petrolatum,
greases, jellies, fumed silica and/or
aluminosilicates, urea, and clay;
Examples of waxes which may be used include Paraffin
Wax distributed by Whittaker, Clark & Daniels, Inc. and
Luwax from BASF, and MULTIWAX Microcrytalline WAX from
Witco. A preferred wax is glyceryl stearate.
Generally, the gelling agent will comprise 1 to 20% by wt.
total composition.

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Bar Moisture Level
Finally, bars of the invention use low levels of water,
i.e., 2% to less than 10% by wt., preferably 2% to 8%, more
preferably 3% to 7% by weight of the total composition.
Water levels are kept purposefully in such a range to ensure
homogenous, pumpable melts which, upon cooling, forth rigid
solids. Excess water will result in poor mixing, low
viscosities and phase separation in the melt and
unacceptably soft solids and mushiness when cooled.
Optional Structuring Aids and Fillers
Another optional component of the invention is the use
of solid structuring aids and fillers, i.e., to maintain bar
structural integrity. Examples of such structuring aids
include, but are not limited to the following:
polyalkylene glycols having MW of 2500 to 10,000 and MP of
about 40~C to 55~C; C8 to CZO alkanols, preferably straight
chain, preferably saturated C14 to C18 alkanols; C8 to Czs
fatty acids, preferably straight chain, preferably saturated
C14 to C22 fatty acids; and water soluble starches, such as
maltodextrin.
The structuring aids and fillers generally comprise 0%
to 35% by weight of the bar composition, preferably 10% to
25% by weight.

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WO 98I16620 PCT/EP97/055?6
- 21 -
Other Optional Ingredients
Other components which may be used in the bars of the
invention are as follows:
Bars of the invention also generally incorporate 0 to
30% by wt., preferably 1 to 25% of a benefit agent in the
bar composition.
The benefit agent "composition" of the subject
invention may be a single benefit agent component or it may
be a benefit agent compound added via a carrier. Further
the benefit agent composition may be a mixture of two or
more compounds one or a11 of which may have a beneficial
aspect. In addition, the benefit agent itself may act as a
carrier for other components one may wish to add to the bar
composition.
The benefit agent can be an "emollient oil" by which is
meant a substance which softens the skin (stratum corneum)
by increasing into water content and keeping it soft by
retarding decrease of water content.
Preferred emollients include:
(a) silicone oils, gums and modifications thereof such
as linear and cyclic polydimethylsiloxanes; amino,
alkyl, alkylaryl and aryl silicone oils;
(b) fats and oils including natural fats and oils such
as jojoba, soybean, rice bran, avocado, almond,
olive, sesame, persic, castor, coconut, mink oils;

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- 22 -
cacao fat; beef tallow, lard; hardened oils
obtained by hydrogenating the aforementioned oils;
and synthetic mono, di and triglycerides such as
myristic acid glyceride and 2-ethylhexanoic acid
glyceride;
(c) waxes such as carnauba, spermaceti, beeswax,
lanolin and derivatives thereof;
(d) hydrophobic plant extracts;
(e) hydrocarbons such as liquid paraffins, vaseline,
microcrystalline wax, ceresin) squalene) pristan
and mineral oil;
(f) higher fatty acids such as lauric, myristic,
palmitic, stearic, behenic, oleic, linoleic,
linolenic, lanolic, isostearic and poly
unsaturated fatty acids (PUFA);
(g) higher alcohols such as lauryl) cetyl, stearyl,
oleyl, behenyl, cholesterol and 2-hexadecanol
alcohol;
(h) esters such as cetyl octanoate, myristyl lactate,
cetyl lactate, isopropyl myristate, myristyl
myristate, isopropyl palmitate, isopropyl adipate,
butyl stearate, decyl oleate, cholesterol
isostearate, glycerol monostearate, glycerol
distearate, glycerol tristearate, alkyl lactate,
alkyl citrate and alkyl tartrate;
(i) essential oils such as mentha, jasmine, camphor,
white cedar, bitter orange peel, ryu, turpentine,
cinnamon, bergamot, citrus unshiu) calamus, pine,
lavender, bay, clove, hiba, eucalyptus, lemon,

CA 02267377 1999-03-31
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- 23 -
starflower, thyme, peppermint, rose, sage,
menthol, cineole, eugenol, citral, citronelle,
borneol, linalool, geraniol, evening primrose,
camphor, thymol, spirantol, penene, limonene and
terpenoid oils;
(j) lipids such as cholesterol, ceramides, sucrose
esters and pseudo-ceramides as described in
European Patent Specification No. 556,957;
(k) vitamins such as vitamin A and E, and vitamin
alkyl esters, including those vitamin C alkyl
esters;
(1) sunscreens such as octyl methoxyl cinnamate
(Parsol MCX) and butyl methoxy benzoylmethane
(Parsol 1789);
(m) phospholipids; and
(n) mixtures of any of the foregoing components.
A particularly preferred benefit agent is silicone,
preferably silicones having viscosity greater than about
10,000 centipoise. The silicone may be a gum and/or it may
be a mixture of silicones. One example is
polydimethylsiloxane having viscosity of about 60,000
centistokes.
A11 percentages mentioned above are intended to be by
wt. unless otherwise indicated.

CA 02267377 1999-03-31
C6440
- 24 -
The following examples are meant for illustrative
purposes only and are not intended to limit the claims in
any way.
EXAMPLES
Methodoloav
Mildness Assessments
Zein dissolution test was used to preliminarily screen
the irritation potential of the formulations studies. In an
225gm (8 oz.) jar, 30 mLs of an aqueous dispersion of a
formulation were prepared. The dispersion sat in a 45'C bath
until fully dissolved. Upon equilibration at room
temperature, 1.5 gms of zero powder were added to each
solution with rapid stirring for one hour. The solutions
were then transferred to centrifuge tubes and centrifuged
for 30 minutes at approximately 3,000 rpms. The undissolved
zero was isolated, rinsed and allowed to dry in a 60'C vacuum
oven to a constant weight. The percent zero solubilized,
which is proportional to irritation potential, was
determined gravimetrically.
Formulation Processing (Cast-melt)
Bars were prepared by a cast melt process. First, the
components were mixed together at 80-120~C in a 500 ml
beaker, and the water level was adjusted to approximately
10-15 wt.~. The batch was covered to prevent moisture loss

CA 02267377 1999-03-31
WO 98/l6620 PCT/EP97/05576
- 25 -
and was mixed for about 15 minutes. Then the cover was
removed, and the mixture was allowed to dry. The moisture
content of the samples taken at different times during the
drying stage and was determined by Karl Fisher titration
with a turbo titrator. At the final moisture level (~5% by
weight), the mixture in the beaker (in the form of a free-
flow liquid) was dropped into bar molds and was allowed to
be cooled at room temperature for four hours. Upon
solidification, the mixture was tasted in the bar mold into
a bar.
EXAMPLE 1
The Impact of PEG !MW > 300) / Anionic Ratio on Anionic
Surfactant - Protein Interaction
In the zein dissolution testing (Figure 1), PEGS with
molecular weight at 400 and above were found to
significantly reduce the amount of zero protein dissolved by
sodium acyl isethionate when the PEG to the anionic
surfactant weight ratio was above 1:1, preferably above 2:1.
Below this 1:1 PEG/anionic ratio, the benefit of zein-
reduction by PEG was insignificant. These results show
that, only at relatively high levels of addition, PEGS
having molecular weight above 300 Dalton, preferably above
about 350, function as skin moisturizer to reduce the
surfactant skin interaction that leads to skin irritation.

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- 26 -
EXAMPLE 2
The Lack of Mildness Enhancement of PEG (MW # 300) on
Anionic Surfactants
At and below molecular weight 300, PEGS and the presented
water soluble nonionic monomers (i.e., ethylene glycol,
propylene glycol, sorbitol, and glyceryl) do not
significantly reduce the amount of zein protein dissolved by
sodium acyl isethionate (Figure 2) and sodium laurylether
(3E0) sulfate (Figure 3). Therefore, there is a cut-off PEG
molecular weight (around 300), below which PEG and those
water soluble monomers are ineffective in reducing the
surfactant protein interaction that may lead to skin
irritation.
EXAMPLE 3
Bar Formulations
The bar formulations 1-4 in Table 1 use anionic sodium
acyl isethionate and sodium laurylether (3E0) sulfate and
amphoteric cocoamidopropyl betaine as the major detergents.
Novel to the art, these bar compositions contain relatively
high levels of low MW PEGS (MW between 400-1500) as
moisturizer. PEG 1450 and PEG1000 in these ultra-mild bars
(Formulation No. 1 to No. 4) promote rich and creamy lather.
Table 1: Bar compositions containing relatively high levels
of low MW PEGs.

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- 27 -
FORMULATIONS
NO. 1 No. 2 No. 3 No. 4
COMPOSITIONS Wt.% Wt.% Wt.% Wt.%
Sodium Acyl 15.0 I5.0 8.0 10.0
Isethionate
Sodium Laurylether 0.0 0.0 2.0 3.0
(3E0) Sulfate
Cocoamidopropyl 10.0 10.0 15.0 12.0
Betaine
Sodium Stearate 12.0 15.0 15.0 9.0
PEG1450 35.5 18.5 40.0 30.0
PEG1000 0.0 0.0 0.0 12.0
PEG8000 15.0 29.0 5.0 7.0
Fatty Acid 4.0 4.0 9.5 4.5
Paraffin Wax 3.0 3.0 0.0 7.0
Water 5.5 5.5 5.5 5.5

Representative Drawing

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Administrative Status

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Event History

Description Date
Inactive: IPC deactivated 2011-07-29
Inactive: Cover page published 2008-07-14
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Time Limit for Reversal Expired 2002-10-01
Application Not Reinstated by Deadline 2002-10-01
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2001-10-01
Amendment Received - Voluntary Amendment 2000-08-09
Letter Sent 2000-02-09
Request for Examination Received 2000-01-11
All Requirements for Examination Determined Compliant 2000-01-11
Request for Examination Requirements Determined Compliant 2000-01-11
Letter Sent 1999-08-10
Inactive: Single transfer 1999-07-14
Inactive: Cover page published 1999-06-07
Inactive: First IPC assigned 1999-05-18
Inactive: IPC assigned 1999-05-18
Inactive: IPC assigned 1999-05-18
Inactive: IPC assigned 1999-05-18
Inactive: Courtesy letter - Evidence 1999-05-11
Inactive: Notice - National entry - No RFE 1999-05-07
Inactive: Applicant deleted 1999-05-05
Application Received - PCT 1999-04-30
Application Published (Open to Public Inspection) 1998-04-23

Abandonment History

Abandonment Date Reason Reinstatement Date
2001-10-01

Maintenance Fee

The last payment was received on 2000-09-18

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

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, 2nd anniv.) - standard 02 1999-10-01 1999-03-31
Basic national fee - standard 1999-03-31
Registration of a document 1999-07-14
Request for examination - standard 2000-01-11
MF (application, 3rd anniv.) - standard 03 2000-10-02 2000-09-18
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
UNILEVER PLC
Past Owners on Record
GEORGIA LYNN SHAFER
JAMES JOSEPH DALTON
KENNARD DANIELS
MENGTAO HE
MICHAEL MASSARO
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 1999-03-31 27 853
Abstract 1999-03-31 2 109
Abstract 1999-03-31 1 53
Claims 1999-03-31 3 72
Drawings 1999-03-31 2 54
Cover Page 1999-06-07 1 40
Notice of National Entry 1999-05-07 1 194
Courtesy - Certificate of registration (related document(s)) 1999-08-10 1 140
Acknowledgement of Request for Examination 2000-02-09 1 180
Courtesy - Abandonment Letter (Maintenance Fee) 2001-10-29 1 183
Correspondence 1999-05-11 1 31
PCT 1999-03-31 13 455