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Patent 2233229 Summary

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(12) Patent: (11) CA 2233229
(54) English Title: FABRIC SOFTENING COMPOSITION
(54) French Title: COMPOSITION ASSOUPLISSANTE POUR TEXTILES
Status: Deemed expired
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11D 3/26 (2006.01)
  • C11D 1/835 (2006.01)
  • C11D 3/22 (2006.01)
  • C11D 1/62 (2006.01)
  • C11D 1/66 (2006.01)
(72) Inventors :
  • TURNER, GRAHAM ANDREW (United Kingdom)
(73) Owners :
  • UNILEVER PLC (United Kingdom)
(71) Applicants :
  • UNILEVER PLC (United Kingdom)
(74) Agent: BERESKIN & PARR LLP/S.E.N.C.R.L.,S.R.L.
(74) Associate agent:
(45) Issued: 2008-04-22
(86) PCT Filing Date: 1996-09-25
(87) Open to Public Inspection: 1997-05-01
Examination requested: 2003-07-28
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP1996/004260
(87) International Publication Number: WO1997/015651
(85) National Entry: 1998-03-26

(30) Application Priority Data:
Application No. Country/Territory Date
9521667.7 United Kingdom 1995-10-23

Abstracts

English Abstract




An aqueous fabric softening composition comprising: (a) a water insoluble,
quaternary ammonium material comprising at least one
ester link and two C12-28 alkyl or alkenyl groups, and (b) a sucrose ester or
an alkyl polyglucoside.


French Abstract

Cette composition aqueuse assouplissante pour textiles comprend: a) un matériau à base d'ammonium quaternaire, insoluble dans l'eau, et comprenant au moins une liaison ester ainsi que deux groupes alkyle ou alcényle C12-28, et b) un ester de saccharose ou un polyglucoside d'alkyle.

Claims

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




-15-
Claims:


1) An aqueous fabric softening composition comprising:
a) a water insoluble, quaternary ammonium material
comprising at least one ester link and two C22-28 alkyl
or alkenyl groups;

b) a nonionic stablilizing agent;

characterised in that the nonionic stabilizing agent
is a mixture of a mono-ester, a di-ester and a tri-
ester sucrose ester and in that the composition
comprises an aqueous dispersion of the water insoluble
quaternary ammonium material

2) A fabric softening composition according to Claim 1 in
which the nonionic stabilising agent comprises from
56 wt% to 75 wt% of sucrose mono-ester.

3) A fabric softening composition according to Claim 1 or
2 in which the level of nonionic stabilising agent is
from 0.1 wt% to 2.5 wt% of the total composition.

4) A fabric softening composition according to Claims 1,
2 or 3 in which the ratio of quaternary ammonium
material to nonionic stabilising agent is in the range
from 5:0.5 to 5:0.1.

5) A fabric softening composition according to any one of
Claims 1 to 4 in which the viscosity of the
composition is in the range from 15mPa.s to 120mPa.s
at a shear rate of 110s-1.



-16-

6) A fabric softening composition according to any one of
Claims 1 to 5 in which the composition further
comprises more than 0.1 wt% of a fatty acid material.
7) A fabric softening composition according to claim 6
in which the fatty acid material is present from
0.25 wt% to 20 wt%.

8) A process for making a liquid fabric softening
composition comprising the steps of selecting the
following ingredients:

a) a water insoluble, quaternary ammonium material
comprising at least one ester link and two C12-28 alkyl
groups;

b) a nonionic stabilising agent which is a sucrose
ester;

then mixing the ingredients whilst heating to form a
melt, followed by dispersing the melt in water, to
form an aqueous dispersion of the water insoluble
quaternary ammonium material.

Description

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



CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 1 -

FAF3RIC SOFTENING COMPOSITION
Field of the Invention
The present invention relates to a fabric softening
composition, in particular the invention relates to aqueous
dispersions of fabric softening compositions comprising a
water insoluble quaternary ammonium material and a nonionic
stabilising agent suitable as rinse-added fabric softener
compositions.

Backaround of the Invention

Rinse added fabric softeners are known. Typically such
compositions contain a water insoluble quaternary ammonium
fabric softening agent dispersed in water at a level of
softening agent up to about 7 wt%, in which case the
compositions are considered dilute, or at levels from 7 wt%
to 50 wt%, in which case the compositions are known as
concentrates.

The viscosity of fabric softener may be seen by the consumer
as an important attribute. For this reason thickening
polymers are added to compositions, for example EP 0 331 237
(Unilever) discloses the use of hydrophobically modified
nonionic cellulose ether for use as a thickener for fabric
conditioning compositions containing quaternary ammonium
cations.
There are however negative attributes associated with many
polymeric thickeners in that they are not biodegradable,
their addition to the rinse product is technically difficult
and the viscosity of such polymer thickened products tends to
increase with time.


CA 02233229 1998-03-26
= C3685 - 2 -

In US 4 137 180 (Lever Brothers Company) discloses cationic
di-esters of the formula

R'COOCHa

CH-CH_-NR;R,R, X-
/
RSCOO

wherein R1, R. and R3 are each an alkyl or hydroxyalkyl group
containing from 1 to 4 carbon atoms, or a benzyl group, R,
and Rsare each alkyl chains containing from 11 to 23 carbon
atoms and X- is a water soluble anion.

One of the problems associated with fabric softening
compositions containing cationic di-esters as disclosed in US
4 137 180 is the physical instability of these compounds, the
problem is exacerbated at temperatures above or below
ambient.
EP 280 550 and EP 507 478 (Unilever) discloses the use of
selected nonionic stabilising agents to overcome the poor
stability. However we have found that many nonionic
stabilising agents create a further problem in that their
presence destroys the viscosity of these fabric softening
compositions.

EP 409 504 (Unilever ) discloses fabric softening
compositions comprising at least 1% w/w of an ester linked
quat and an extruder material which can be esters of
predominantly linear Ca-C28 fatty acids with polyhydric
alcohols.

AMENDED SHSEi'


CA 02233229 1998-03-26
C3685 -
- 2a -

WO 95/27777 discloses rinse conditioners comprising a fabric
softening compound and a solubilising agent to be coated
onto a tufible dryer sheet.

We have now found that selected nonionic stabilising agents
do not destroy the viscosity of fabric softening compositions
containing a biodegradable quaternary ammonium material.
Description of the Invention

Accordingly the present invention relates to a fabric
softening composition comprising:

~-.

AMENDED SHEET


CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 3 -

a) a water insoluble, quaternary ammonium material
comprising one ester link and two C12_28 alkyl or alkenyl
groups;

} 5 b) a nonionic stabilising agent;

characterised in that the nonionic stabilising agent is a
sucrose ester or an alkyl polyglucoside.

Further disclosed is a process for making a liquid fabric
softening composition comprising the steps of selecting the
following ingredients:

a) a water insoluble, quaternary ammonium material having
at least one ester link and two C12_28 alkyl or alkenyl
groups;

b) a nonionic stabilising agent which is either a sucrose
ester or an alkyl polyglucoside;
c) other optional ingredients;

mixing the ingredients whilst heating to form a melt,
followed by dispersing the melt in hot water to give the
rinse conditioner.

Detailed Describtion of the Invention

The present invention is a way of controlling the viscosity
of a fabric conditioner composition containing a
biodegradable quaternary ammonium material and a nonionic
stabilising agent. Suitable nonionic stabilising agents
include the sucrose esters such as sucrose distearate and
sucrose monostearate, and the alkyl polyglucosides such as
stearyl monoglucosides and stearyl triglucoside.


CA 02233229 1998-03-26
WO 97/15651 PCT/EP96/04260
- 4 -

Without wishing to bound by theory, this invention is thought
to operate in that the interaction of the hydrogen bonding
elements of the molecules of the nonionic stabilising agent
are essential to maintain a vesicular structure. A vesicular
structure in the context of this invention can be defined as
a spherical structure having onion ring shaped bilayers. The
presence of such vesicular structures are an important
factor in the formation of a composition with a commercially
acceptable viscosity.
The preferred level of nonionic stabilising agent present is
0.1 to 2.5 % by weight.

Most preferred nonionic stabilising agents are the sucrose
esters. The sucrose esters have the additional benefit that
they impart additional softening benefits over the cationic
softening agent. Examples of suitable sucrose esters include
the Crodesta (Trademark (ex Croda)) series. Crodestas are
sucrose esters esterified with 70/30 mixture of
stearic/palmitic acid to form a mixes of mono-ester, di-ester
and triester. According to.the manufacturer the levels of
mono-ester are as follows:


CA 02233229 1998-03-26

WO 97/15651 PCT/EP96104260
- 5 -

Trade Name wt % monoester
Crodesta F10 3
Crodesta F20 10
Crodesta F50 29
Crodesta F70 56
Crodesta F110 52
Crodesta F140 57
Crodesta F160 - 75
We have found that these combination of mono-esters and di-
esters and triesters of sucrose give particularly good
softening benefits. Especially preferred are combinations of
mono-ester, di-ester and triester that contain 56-75%
monoester, in particular Crodesta F160, Crodesta F140,
Crodesta 110 and Crodesta F70.

The fabric softening compound is suitably a substantially
water insoluble quaternary ammonium material comprising a
polar head group and two alkyl or alkenyl chains each having
an average chain length greater than or equal to C14, and at
least one ester group.

Preferably the fabric softening compound of the invention has
two long chain alkyl or alkenyl chains, each having an
average chain length greater than or equal to C16. Most
preferably at least 50% of each long chain alkyl or alkenyl
group has a chain of C.

It is preferred if the long chain alkyl or alkenyl groups of
the fabric softening compound are predominantly linear.

The fabric softening compounds used in the compositions of
the invention are molecules which provide excellent


CA 02233229 1998-03-26
WO 97/15651 PCT/EP96/04260
- 6 -

softening, and characterised by a chain melting -LP to LOG -
transition temperature greater than 25 C, preferably greater
than 35 C, most preferably greater than 45 C. This Lp to La
transition can be measured by DSC as defined in "Handbook of
ti
Lipod Bilayers, D Marsh, CRS Press, Boca Raton Florida, 1990
(Pages 137 and 337).

Substantially insoluble fabric softening compounds in the
context of this invention are defined as fabric softening
compounds having a solubility less than 1 x 10-3 wt% in
demineralised water at 20 C. Preferably the fabric softening
compounds have a solubility less than 1 x 10-4. Most
preferably the fabric softening compounds have a solubility
at 20 C in demineralised water from 1 x 10-8 to 1 x 10'6.
It is especially preferred if the fabric softening compound
is a water insoluble quaternary ammonium material which
comprises a compound having two C1._la alkyl or alkenyl groups
connected to the molecule via at least one ester link. It is
more preferred if the quaternary ammonium material has two
ester links present. An especially preferred ester-linked
quaternary ammonium material for use in the invention can be
represented by the formula:

R'
I
R' = N' (CH,) n-T-R2 X'
I
(CH; ) ,,-T-R'
wherein each R1 group is independently selected from C1_4
alkyl, hydroxyalkyl or C1_, alkenyl groups; and wherein each
R= group is independently selected from C$_a8 alkyl or alkenyl
groups; X- is any suitable anion. 35


CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 7 -

0 0
T is -O-C- or -C-O-; and
n is an integer from 0-5.
Di(tallowyloxyethyl) dimethyl ammonium chloride is especially
preferred.

A second preferred type of quaternary ammonium material can
be represented by the formula

OOCR'
( R1) 3N' - (CH2 ) n CH X-
CH2O O CRZ

wherein R1, X-, n and R 2 are as defined above.

Preferred materials of this class such as 1,2 bis[hardened
tallowoyloxy]-3- trimethylammonium propane chloride and their
method of preparation are, for example, described in
US 4 137 180 (Lever Brothers). Preferably these materials
comprise small amounts of the corresponding monoester as
described in US 4 137 180 for example 1-hardened
tallowoyloxy-2-hydroxy-3- trimethylammonium propane chloride.
It is preferred if the quaternary ammonium compound is
biodegradable. Biodegradable in the context of this
invention should be interpreted as meaning degrades to
materials that are not known to be harmful to the
environment.



CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 8 - -

The ratio of quaternary ammonium material to nonionic
stabilising agent is in the range from 5:0.5 to 5:0.1.
The composition may also contain long chain fatty acid
material for example C8 - Caq alkyl or alkenyl monocarboxylic
acids or polymers thereof. Preferably saturated fatty acids
are used, in particular hardened tallow C16 - C18 fatty acids.
Preferably the fatty acid is non-saponified, more preferably
the fatty acid is free for example oleic acid. lauric acid or
tallow fatty acid.

The level of fatty acid material is preferably more than
0.1%, more preferably more than 0.2% by weight. Especially
preferred are dilutes in which the fatty acid material is
present from 0.25 wt% to 20 wt%. The weight ratio of
quaternary ammonium compound to fatty acid material is
preferably from 1:10 to 10:1.

It is desirable if the viscosities of these fabric
compositions lie in the range from 15 mPa.s to 120 mPa.s at
a shear rate of 110s-1.

The compositions of the invention preferably have a pH of
more than 2, more preferably between 2 and S.
The composition-can also contain one or more optional
ingredients, selected from the group consisting of non-
aqueous solvents, pH buffering agents, perfumes, perfume
carriers, fluorescers, colorants, hydrotopes, antifoaming
agents, antiredeposition agents, enzymes, optical
brighteners, opacifiers, antishrinking agents, drape
imparting agents, antistatic agents and ironing aids.

The composition may also contain nonionic fabric softening
agents such as lanolin and derivatives thereof.


CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 9 -

The invention will now be illustrated by the following non-
limiting examples.

EXAMPLES

in the examples all percentages are expressed by weight.
Comparative examples are represented by a letter while
examples of the invention are represented by a number.

In the Examples HEQ is 1,2 bis[hardened tallowoyloxy]-3-
trimethylammonium propane chloride ex Hoechst.

Preparation of Fa]2ric Conditionina Composition

Liquid fabric softening agents were made up as follows:

The cationic fabric softening agent and/or fatty acid and/or
nonionic stabilising agent where appropriate were premixed
and heated together to form a clear melt. The molten mixture
thus formed was added over a period of at least one minute to
water at 70 C to 80 C with constant stirring to form a
dispersion.


CA 02233229 2007-05-22
_ ~ .

- 10 -
S (i g Co_a ity.Mansr P~ t s

Viscosity was measured using the Haakem RV20 Rotov.i3cometer.
Viscosity is quoted ac a shear rate of 10s''. The Casson data
are obtained by using the Casson relationship:

T0.5_T0 D0.3
Where:

= Shear Stress (Pa)
TQ
= Yield Stress (Pa)

= infinite shear rate viscosity (raPa.s)
D
= Shear rate (s'' )

The Casson data were generated using the Haake RV20
Rotoviscometer with a range of shear rates from 0-1000s''.
F-xam,,.n1 _2 Conibaratiye Examolga A-D

Compositions were prepared in which an aqueous dispersion of
5t 6:1 HEQ:fatty acid, 0.5% of the following nonionics were
added:


CA 02233229 2007-05-22
~

- IZ -
T bel

Example Nonionic
A No nonionic
B Genapol" T-150
C Tween" 80
D Tween 85

1 Crodesta F50
2 Crodesta F110
Genapol, Tween and Crodesta are trade marks.

The effect of nonionic type on viscosity of a dilute
quaternary ammonium compound is shown in Table 2.

Table 2

Example 1i,o (mPa . s) (1I.(mpa.g) ICcament.
A 66 14.2 Vesicular
B 26 4.6 No vesicles

C 15 5.4 No vesicles
D 16 8.4 No vesicles
1 87 22.0 Vesicles
2 48 12.3 Vesicles

It can be seen that in the absence of nonionic the
composition has a vesicular structure and accordingly has an
acceptable viscosity. However the presence of nonionics
stabilising agents which are not as specified by this
invention, such as Genapol T-150, Tween 80 and
'I*ween 85, do not allow vesicle formation and hence the
viscosity of the composition is unacceptably low. The
examples according to the invention allow vesicle formation
and so have an acceptably high viscosity.


CA 02233229 1998-03-26
WO 97/15651 PCT/EP96/04260
- 12 -

Co=arat i ve Examnl .s E-G

Compositions were prepared in which 0.5% of the following
nonionic were placed in a composition containing an aqueous
dispersion of 5% 6:1 dihardened tallow dimethyl ammonium
chloride:fatty acid.

Example E No nonionic
Example F Genapol T-150
Example G Crodesta F50

The results are shown in Table 3.
Table 3

Example T1110(mPa.s) Tl..(mPa.s) Comments
E 184 21.8 Vesicular
F 238 10.9 Vesicular
G --- ---- Vesicular
Table 3 demonstrates that nonionic stabilising agents do not
destroy the viscosity in formulations containing dihardened
tallow dimethyl ammonium chloride.
Examnles 3-10 Comoarative Exambles A-B

To a base formulation of 5% HEQ:Hardened tallow fatty acid
6:1 in water the following nonionic stabilising agents were
added:


CA 02233229 1998-03-26

WO 97/15651 PCT/EP96/04260
- 13 -

= Example 3 0.25 % Crodesta F160
Example 4 0.50 % Crodesta F160
Example 5 0.50 % Crodesta F10
Example 6 0.50 % Crodesta F20
Example 7 0.50 % Crodesta F50
Example 8 0.50% Crodesta F70
Example 9 0.50% Crodesta F110
Example 10 0.50 % Crodesta F160

The softening performance of the sugar esters are
demonstrated by Table 4.

Table 4

Examples SScore Total Votes
3 0.8828 31
4 1.0750 37
A 0.0000 6
B 0.5862 22
95% significance is obtained with a difference (A) between
products of 0.9041. 90% significance is obtained when
A=0.7565. it is thus demonstrated that the sucrose esters
exhibit a significant softening benefit.
Table 5 demonstrates the optimum level of mono-ester present
to maximise the softening effect.


CA 02233229 1998-03-26
WO 97/15651 PCT/EP96/04260
- 14 -

Table 5 '

F.2rsLm2jo Softenina Score yotes
0.0000 17
6 0.1689 25
7 0.2136 27
8 0.9444 54
9 1.3931 71
10 0.7005 46

Representative Drawing

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Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date 2008-04-22
(86) PCT Filing Date 1996-09-25
(87) PCT Publication Date 1997-05-01
(85) National Entry 1998-03-26
Examination Requested 2003-07-28
(45) Issued 2008-04-22
Deemed Expired 2016-09-26

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Registration of a document - section 124 $100.00 1998-03-26
Application Fee $300.00 1998-03-26
Maintenance Fee - Application - New Act 2 1998-09-25 $100.00 1998-03-26
Maintenance Fee - Application - New Act 3 1999-09-27 $100.00 1999-08-16
Maintenance Fee - Application - New Act 4 2000-09-25 $100.00 2000-08-16
Maintenance Fee - Application - New Act 5 2001-09-25 $150.00 2001-08-16
Maintenance Fee - Application - New Act 6 2002-09-25 $150.00 2002-09-05
Request for Examination $400.00 2003-07-28
Maintenance Fee - Application - New Act 7 2003-09-25 $150.00 2003-09-17
Maintenance Fee - Application - New Act 8 2004-09-27 $200.00 2004-09-09
Maintenance Fee - Application - New Act 9 2005-09-26 $200.00 2005-09-08
Maintenance Fee - Application - New Act 10 2006-09-25 $250.00 2006-09-07
Maintenance Fee - Application - New Act 11 2007-09-25 $250.00 2007-09-11
Final Fee $300.00 2008-02-06
Maintenance Fee - Patent - New Act 12 2008-09-25 $250.00 2008-08-29
Maintenance Fee - Patent - New Act 13 2009-09-25 $250.00 2009-09-02
Maintenance Fee - Patent - New Act 14 2010-09-27 $250.00 2010-08-30
Maintenance Fee - Patent - New Act 15 2011-09-26 $450.00 2011-08-30
Maintenance Fee - Patent - New Act 16 2012-09-25 $450.00 2012-08-30
Maintenance Fee - Patent - New Act 17 2013-09-25 $450.00 2013-08-30
Maintenance Fee - Patent - New Act 18 2014-09-25 $450.00 2014-09-22
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
UNILEVER PLC
Past Owners on Record
TURNER, GRAHAM ANDREW
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) 
Abstract 1998-03-26 1 41
Cover Page 2008-03-27 1 26
Description 1998-03-26 15 426
Claims 1998-03-26 2 55
Cover Page 1998-07-22 1 23
Description 2007-05-22 15 429
Claims 2007-05-22 2 45
Assignment 1998-03-26 3 146
PCT 1998-03-26 13 410
Prosecution-Amendment 2003-07-28 1 32
Prosecution-Amendment 2004-01-20 1 42
Prosecution-Amendment 2006-11-22 3 120
Prosecution-Amendment 2007-05-22 7 181
Correspondence 2008-02-06 1 28