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Patent 2227341 Summary

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(12) Patent Application: (11) CA 2227341
(54) English Title: FABRIC SOFTENERS CONTAINING WATER SOLUBLE DYES FOR REDUCED STAINING
(54) French Title: AGENTS ADOUCISSANTS CONTENANT DES COLORANTS HYDROSOLUBLES POUR TACHAGE REDUIT
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • C11D 03/40 (2006.01)
  • C11D 01/38 (2006.01)
  • C11D 03/00 (2006.01)
(72) Inventors :
  • DE PAUW, JACQUY (Belgium)
  • ENGELS, KAREL (Belgium)
  • LECLUYSE, DOMINIQUE (Belgium)
  • PEROT, DIDIER (Belgium)
(73) Owners :
  • THE PROCTER & GAMBLE COMPANY
(71) Applicants :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(74) Agent: DIMOCK STRATTON LLP
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1996-06-25
(87) Open to Public Inspection: 1997-02-06
Examination requested: 1998-01-19
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/US1996/001843
(87) International Publication Number: US1996001843
(85) National Entry: 1998-01-19

(30) Application Priority Data:
Application No. Country/Territory Date
95202003.0 (European Patent Office (EPO)) 1995-07-20

Abstracts

English Abstract


The current invention relates to a fabric softener composition comprising: (a) from 1 % to 50 % by weight of a fabric softener active
compound and (b) a water soluble dye system characterized in that the dye system comprises a dye selected from the group consisting of:
1) quinoline yellow 70 with color index No. 47005; 2) tartrazine XX90 with color index No. 19140; 3) orange RGL90 with color index
No. 15985; 4) ponceau 4RC82 with color index No. 16255; 5) blue AE85 with color index No. 42090; 6) patent blue V85/V50 with color
index No. 42051; and 7) mixtures thereof.


French Abstract

La présente invention concerne une composition d'agent adoucissant pour tissus comprenant : (a) de 1 % à 50 % en poids d'un composé actif adoucissant et (b) un système de colorants hydrosolubles caractérisé par le fait que le système de colorants comprend un colorant choisi parmi le groupe suivant : 1) jaune de quinoléine 70, numéro CI (Color Index) 47005; 2) tartrazine XX90, numéro CI 19140; 3) orange RGL90, numéro CI 15985; 4) ponceau 4RC82, numéro CI 16255; 5) bleu AE85, numéro CI 42090; 6) bleu patenté V85/V50, numéro CI 42051; et 7) des mélanges de ces derniers.

Claims

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


23
WHAT IS CLAIMED IS:
1. A fabric softener composition comprising :
(a) from 1% to 50% by weight of a fabric softener active
compound and
(b) a water soluble dye system characterized in that the
dye system comprises a dye selected from the group
consisting of :
1. Quinoline Yellow 70 with color index no. 47005;
2. Tartrazine XX90 with color index no. 19140;
3. Orange RGL90 with color index no. 15985;
4. Ponceau 4RC82 with color index no. 16255;
5. Blue AE85 with color index no. 42090;
6. Patent Blue V85/V50 with color index no. 42051; and
7. mixtures thereof.
2. A fabric softener composition according to claim 1
wherein the dyes are present from 0.1ppm to 1000 ppm,
preferably from 1ppm to 100ppm.
3. A fabric softener composition according to claim 1 or 2
wherein the ratio of the dyes present are from 19:1 to
1:19.
4. A fabric softener composition according to claim 1
wherein the dye system consists of
a)4 parts Patent Blue V85/V50 with color index no. 42051
and 1 part Ponceau 4RC82 with color index no. 16255 or
b)4 parts Blue AE85 with color index no. 42090 and 1 part
Ponceau 4RC82 with color index no. 16255.
5. A fabric softener composition according to claim 1
wherein the dye system consists of
a) Tartrazine XX90 with color index no. 19140 or
b) Quinoline Yellow 70 with color index no. 47005.

24
6. A fabric softener composition according to claim 1
wherein the dye system consists of
a) 2 parts Patent Blue V85/V50 with color index no. 42051
and 3 parts Tartrazine XX90 with color index no. 19140
or
b) 2 parts Patent Blue V85/V50 with color index no. 42051
and 3 parts Quinoline Yellow 70 with color index no.
47005 or
c) 2 parts Blue AE85 with color index no. 42090 and 3 parts
Tartrazine XX90 with color index no. 19140, or
d) 2 parts Blue AE85 with color index no. 42090 and 3 parts
Quinoline Yellow 70 with color index no. 47005.
7. A fabric softener composition according to claim 1
wherein the dye system consists of
a) 1 part Tartrazine XX90 with color index no. 19140 and 1
part Ponceau 4RC82 with color index no. 16255, or
b) 1 part Quinoline Yellow 70 with color index no. 47005
and 1 part Ponceau 4RC82 with color index nol 16255.
8. A fabric softener composition according to claim 1
wherein the dye is mixed with a conventional dye selected
from the group consisting of :
1. Acid Red 52 with color index no. 45100;
2. Acid Yellow 3 with color index no. 47005;
3. Acid Blue 127 with color index no. 61135;
4. Acid Blue 5 with color index nol 42051;
5. Acid Blue 80 with color index no. 61585; and
6. mixtures thereof.
9. A fabric softening composition according to claim 8
wherein the dye system consists of :
a) 2 parts Patent Blue V85/V50 with color index no. 42051
and 3 parts Acid Red 52 with color index no. 45100, or
b) 2 parts Blue AE85 with color index no. 42090 and 3 parts
Acid Red 52 with color index no. 45100.

10. A fabric softener composition according to any of the
preceding claims wherein the pH of the composition is from
1.8 to 6, preferably from 1.8 to 3.5.

Description

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


CA 02227341 1998-01-19
WO 97/04068 PCT/US96/1~1843
FABR]:C SOFTENERS CONTAINING WATER SOLUBLE
D~!ES FOR REDUCED STAINING
~ Technical Field
The present invention relates to the selection of
certain water soluble dyes to be incorporated into liquid
fabric softener compositions to reduce staining of fabrics.
Background of the Invention
Liquid fabric softening compositions have long been
known in the art and are widely utilized by consumers
during the rinse cycles of automatic laundry operations.
The term "fabric softening" as used herein and as known in
the art refers to a process whereby a desirably soft hand
and fluffy appearance are imparted to fabrics.
Dyes are often used in consumer products to provide
pleasing aesthetics. In the case of fabric care products,
one wants to be able to provide the desired color
aesthetics with as little dye as possible to mi~imi ze
chances for staining clothes. Thus, one likes to be able to
formulate with as low a level of dye as possible, yet
provide a pleasant color aesthetic.
In WO 94/10285 is disclosed fabric softening
compositions comprising a dye system with water soluble
LiquitintR dyes. LiquitintR dyes, available from Milliken
Chemical Co., also reduce staining as disclosed in said WO
94/10285, however a disadvantage of LiquitintR dyes is its
color strength. It appears that the color strength of
LiquitintR is very low and thus in order to obtain a
satisfactory level of colorant in a finished fabric

CA 0222734l Isss-ol-ls
W097/04068 PCT~S96/10843
softener product, one need to add high amounts of said
LiquitintR dye.
In case a consumer spills the fabric softener product
containing this LiquitintR dye onto a fabric, unacceptable
st~ining problems occur. Subsequently, the consumer had to
wash the fabric several times in order to remove the stain
and often it turned out not to have the desired results
viz. removal of the stain.
Therefore a new dye system is certainly needed to meet
consumer acceptance regarding this problem. A solution to
this problem is found in the present invention based on the
discovery that water soluble dyes VitasynR, which are
availabie from Hoechst, reduce staining via an increased
ease of stain removal from fabrics.
Said water soluble dyes when applied in fabric softening
compositions also give less hueing than with conventional
dyes.
Said VitasynR dyes are known as colorants in food,
however nowhere is disclosed that VitasynR dyes can be used
in liquid fabric softener compositions leading to a reduced
staining potential. In addition, it appears that the
presence of VitasynR dyes in the fabric softener
compositions surprisingly also leads to less hueing on
fabrics.
Summary of the Invention
The present invention relates to fabric softener
compositions especially liquid fabric softener
compositions, comprising a water soluble dye system. This
dye system comprises dyes selected from the group
consisting of :
1. Quinoline Yellow 70 with color index no. 47005;
2. Tartrazine XX90 with color index no. 19140;
3. Orange RGL90 with color index no. 15985;

CA 02227341 1998-01-19
WO 97/04068 PCT/US96/la843
4. Ponceau 4RC82 with color index no. 16255;
5. Blue AE85 with color index no. 42090;
6. Patent Blue V85/V50 with color index no. 420S1;
7. Green LFS;
8. Green LFS 01; and
9. mixtures thereof.
Most preferred in a composition are the combinations -
of VitasynR dyes Patent Blue V85 and Ponceau or Patent Blue
AE85 and Ponceau.
Said dyes are to be mixed at a certain level and ratio viz.
the dyes are present from 0.lppm to 1000 ppm, preferably
from lppm to 100ppm while the ratio of the present dyes
ranges from 19:1 to 1:19.
De~ailed description of the Invention
The present invention is concerned with fabric
softener compositions comprising
(a) from 1~ to 50% by weight of a fabric softener active
compound and
(b) a water soluble dye system characterized in that the
dye system comprises a dye selected from the group
consisting of :
1. Quinoline Yellow 70 with color index no. 47005;
2. Tartrazine XX90 with color index no. 19140;
3. Orange RGL90 with color index no. 15985;
4. Ponceau 4RC82 with color index no. 16255;
5. Blue A~85 with color index no. 42090;
6. Patent Blue V85/V50 with color index no. 42051; and
7. mixtures thereof.
.
Preferably the dye system consists of
a)4 parts Patent Blue V85/V50 with color index no. 42051
and 1 part Ponceau 4RC82 with color index no. 16255 or

CA 02227341 Iggs-ol-ls
W097/04068 PCT~S96tlO843
b)4 parts Blue AE85 with color index no. 42090 and 1 part
Ponceau 4RC82 with color index no. 16255.
Other preferred dye systems depending on the desired
color to be obtained are
1) a system consisting of
a) Tartrazine XX90 with color index no. 19140 or
b) Quinoline Yellow 70 with color index no. 47005.
2) a system consisting of
a)2 parts Patent Blue V85/V50 with color index no. 42051
and 3 parts Tartrazine XX90 with color index no. 19140
or
b)2 parts Patent Blue V85/V50 with color index no. 42051
and 3 parts Quinoline Yellow 70 with color index no.
47005 or
c)2 parts Blue AE85 with color index no. 42090 and 3
parts Tartrazine XX90 with color index no. 19140, or
d)2 parts Blue AE85 with color index no. 42090 and 3
parts Quinoline Yellow 70 with color index no. 47005.
3) a system consisting of
a)1 part Tartrazine XX90 with color index no. 19140 and
1 part Ponceau 4RC82 with color index no. 16255, or
b)l part Quinoline Yellow 70 with color index no. 47005
and 1 part Ponceau 4RC82 with color index no. 16255.
The dyes according to the invention can also be mixed
with other commercially available conventional dyes which
are for instance Acid Red 52 with color index no. 45100,
Acid Yellow 3 with color index no. 47005, Acid Blue 127
with color index no. 61135, Acid Blue 5 with color index
no. 42051, Acid Blue 80 with color index no. 61585 and
mixtures thereof.
Furthermore, the pH of the composition is less than
about 6, preferably less than about 4 and more preferably
from 1.8 to 3.5.
_ _ _ _ _ _

CA 02227341 lsss-ol-lg
W097/04068 PCT~S96/10843
For example, 2 parts Patent Blue V85/V50 can be mixed
with 3 parts Acid Red 52 or 2 parts Blue AE85 can be mixed
with 3 parts Acid Red 52.
The VitasynR dyes, above mentioned according to the
invention, are highly water-soluble. So a high color
intensity is possible because of the high color strength of
the VitasynR dyes itself. Consequently only small amounts
of the respective VitasynR dye is needed to obtain the
desired color in the finished fabric softening product.
The dyes are water soluble and non-reactive and are
therefore compatible with fragrances and preservatives and
tend not to complex with other usual ingredients of the
composition.
The dyes are stable in a wide pH range, especially at a
lower pH in the range of 1.8 to 3.5 which is important in
especially biodegradable softener compositions.
The dyes can be added to the composition at any point
during the processing including into the water seat, after
the addition of electrolyte (hot) or post-addition to the
cooled product or mixed with any other raw material prior
to the addition into the final mix.
The fabric softeners
Fabric conditioning compositions, in particular fabric
softening compositions to be used in the rinse cycle of
laundry washing processes, are well known.
The fabric softening materials may be selected from
~ cationic, nonionic, amphoteric or anionic fabric softening
material.
Compositions of the present invention preferably
comprise from 1 to 80% by weight of fabric softening

CA 02227341 1998-01-19
W097/04068 PCT~S96/10843
active, more preferably from 2 to 70% by weight, most
preferably from 5 to 50~ by weight of the composition.
Typically, such compositions contain a water-insoluble
~uaternary-ammonium fabric softening active, the most
commonly used having been di-long alkyl chain ammonium
chloride.
In recent years, the need has arisen for more
environmentally-friendly materials, and rapidly
biodegradable quaternary ammonium compounds have been
presented as alternatives to the traditionaly used di-long
chain ammonium chlorides. Such quaternary ammonium
compounds contain long chain alk~en)yl groups interrupted
by functional groups such as carboxy groups.
Said materials and fabric softening compositions
containing them are disclosed in numerous publications such
as EPA 040 562, and EPA 239 9lO.
In EPA 239 9lO, it has been disclosed that a pH range
of from 2.5 to 4.2 provides optimum storage stability to
said rapidly biodegradable ammonium compounds.
The quaternary ammonium compounds and amine precursors
herein have the formula (I) or (II), below :
R \ /R2 R \ /R3
X Rl (CH2) - Q-T1 or N~ CH2~ -IH- 1~2 X
(I) (II)
O O O O O

CA 02227341 1998-01-19 ,.
WO 97/04068 PCT/US96/1(D843
Il 11 11 11 11
Q is -O-C- or -C-O- or -O-C-O- or -NR4-C- or -C-
NR4-;
1 is (CH2)n-Q-T2 or T3;
R2 is (CH2)m-Q-T4 or T5 or R3;
R3 is C1-C4 alkyl or C1-C4 hydroxyalkyl or H;
R4 is H or C1-C4 alkyl or C1-C4 hydroxyalkyl;
T1, T2, T3, T4, T5 are (the same or different) C11-C22
alkyl or alkenyl;
n and m are integers from 1 to 4; and
X~ is a softener-compatible anion.
The alkyl, or alkenyl, chain Tl, T2, T3, T4, T5 must
contain at least 11 carbon atoms, preferably at least 16
carbon atoms. The chain may be straight or branched.
Tallow is a convenient and inexpensive source of lony
chain alkyl and alkenyl material. The compounds wherein
T1, T2, T3, T4, T5 represents the mixture of long chain
materials typical for tallow are particularly preferred.
Specific examples of quaternary ammonium compounds
suitable for use in the aqueous fabric softening
compositions herein include :
1) N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethylammonium
chloride;
2) N,N-di(tallowoyl-oxy-ethyl)-N-methyl, N-(2-
hydroxyethyl);
3) N,N-di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium
chloride;
4) N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethyl
ammonium chloride;
5) N-(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-
ethyl)-N,N-dimethyl ammonium chloride;
6) N,N,N-tri(tallowyl-oxy-ethyl)-N-methyl
ammonium chloride;

CA 02227341 1998-01-19
W097/04068 PCT~S96/10843
7) N-(2-tallowyloxy-2-oxoethyl~-N-(tallowyl-N,N-dimethyl-
ammonium chloride; and
8) l,2-ditallowyl oxy-3-trimethylammoniopropane chloride.;
and mixtures of any of the above materials.
Of these, compounds 1-7 are examples of compounds of
Formula (I); compound 8 is a compound of Formula (II).
Particularly preferred is N,N-di(tallowoyl-oxy-ethyl)-
N,N-dimethyl ammonium chloride, where the tallow chains are
at least partially unsaturated.
The level of unsaturation of the tallow chain can be
measured by the Iodine Value (IV) of the corresponding
fatty acid, which in the present case should preferably be
in the range of from 5 to l00 with two categories of
compounds being distinguished, having a IV below or above
25.
Indeed, for compounds of Formula (I) made from tallow
fatty acids having a IV of from 5 to 25, preferably 15 to
20, it has been found that a cis/trans isomer weight ratio
greater than about 30/70, preferably greater than about
50/50 and more preferably greater than about 70/30 provides
optimal concentrability.
For compounds of Formula (I) made from tallow fatty acids
having a IV of above 25, the ratio of cis to trans isomers
has been found to be less critical unless very high
concentrations are needed.
Other examples of suitable quaternary ammoniums of
Formula (I) and (II) are obtained by, e.g. :
- replacing ~Itallow'' in the above compounds with, for
example, coco, palm, lauryl, oleyl, ricinoleyl, stearyl,
palmityl, or the like, said fatty acyl chains being
either fully saturated, or preferably at least partly
unsaturated;
- replacing "methyl" in the above compounds with ethyl,
ethoxy, propyl, propoxy, isopropyl, butyl, isobutyl or t-
butyl;

CA 02227341 1998-01-19
WO 97/04068 PCT/US96/10843
- replacing "chloride" in the above compounds with bromide,
methylsulfate, formate, sulfate, nitrate, and the like.
In fact, the anion is merely present as a counterion of
the positively charged quaternary ammonium compounds. The
nature of the counterion is not critical at all to the
practice of the present invention. The scope of this
invention is not considered limited to any particular
anion.
By "amine precursors thereof" is meant the secondary or
tertiary amines corresponding to the above quaternary
ammonium compounds, said amines being substantially
protonated in the present compositions due to the claimed
pH values.
The quaternary ammonium or amine precursors compounds
herein are present at levels of from about 1% to about 80%
of compositions herein, depending on the composition
execution which can be dilute with a preferred level of
active from about 5% to about 15%, or concentrated, with a
preferred level of active from about 15~ to about 50%, most
preferably about 15% to about 35%.
Optional ingredients
Fully formulated fabric softening compositions can
contain polymers having a partial or net cationic charge.
Such polymers can be used at levels of from 0.001% to
10%, preferably 0.01% to 2% by weight of the compositions.
Such polymers having a partial cationic charge can be
polyamine N-oxide containing polymers which contain units
having the following structure formula (A):
p
I
(AJ Ax
I
R

CA 02227341 1998-01-19
WO 97/04068 PCI~/US96/10843
wherein P is a polymerisable unit, whereto the R-N~O
group can be attached to or wherein the R-N~O group forms
part of the polymerisable unit or a combination of both.
O O O
Il 11 11
A is -NC-, -CO-, -C-, -O-, -S-, -N- ; x is 0 or 1;
R are aliphatic, ethoxylated aliphatics, aromatic,
heterocyclic or alicyclic groups or any combination thereof
whereto the nitrogen of the N~O group can be attached or
wherein the nitrogen of the N~O group is part of these
groups.
The N~O group can be represented by the following
general structures :
O O
~R~ ~)y ----N--~R)x
(~3)z
wherein R1, R2, and R3 are aliphatic groups, aromatic,
heterocyclic or alicyclic groups or combinations thereof, x
or/and y or/and z is 0 or 1 and wherein the nitrogen of the
N~O group can be attached or wherein the nitrogen of the N
~O group forms part of these groups.
The N~O group can be part of the polymerisable unit (P)
or can be attached to the polymeric backbone or a
combination of both.
Suitable polyamine N-oxides wherein the N~O group forms
part of the polymerisable unit comprise polyamine N-oxides
wherein R is selected from aliphatic, aromatic, alicyclic
or heterocyclic groups.
One class of said polyamine N-oxides comprises the group
of polyamine N-oxides wherein the nitrogen of the N~O
group forms part of the R-group. Preferred polyamine N-
oxides are those wherein R is a heterocyclic group such as
pyrridine, pyrrole, imidazole, pyrrolidine, piperidine,
quinoline, acridine and derivatives thereof.

CA 02227341 1998-01-19
WO 97/04068 PCT/US96/10843
11
Another class of said polyamine N-oxides comprises the
group of polyamine N-oxides wherein the nitrogen of the N-
~O group is attached to the R-group.
Other suitable polyamine N-oxides are the polyamine
oxides whereto the N~O group is attached to the
polymerisable unit.
Preferred class of these polyamine N-oxides are the
polyamine N-oxides having the general formula (A) wherein R
is an aromatic, heterocyclic or alicyclic groups wherein
the nitrogen of the N~O functional group is part of said R
group.
Examples of these classes are polyamine oxides wherein R
is a heterocyclic compound such as pyrridine, pyrrole,
imidazole and derivatives thereof.
Another preferred class of polyamine N-oxides are the
polyamine oxides having the general formula (A) wherein R
are aromatic, heterocyclic or alicyclic groups wherein the
nitrogen of the N~o functional group is attached to said R
groups.
Examples of these classes are polyamine oxides wherein R
groups can be aromatic such as phenyl.
Any polymer backbone can be used as long as the amine
oxide polymer formed is water-soluble and has dye transfer
inhibiting properties. Examples of suitable polymeric
backbones are polyvinyls, polyalkylenes, polyesters,
polyethers, polyamide, polyimides, polyacrylates and
mixtures thereof.
The amine N-oxide polymers useful herein typically have a
ratio of amine to the amine N-oxide of about 10:1 to about
1:1000000. However the amount of amine oxide groups present
in the polyamine N-oxide cont~;n;ng polymer can be varied
by appropriate copolymerization or by appropriate degree of
N-oxidation. Preferably, the ratio of amine to amine N-
oxide is from about 2:3 to about 1:1000000. More preferably
from about 1:4 to about 1:1000000, most preferably from
about 1:7 to about 1:1000000. The polymers of the present
invention actually encompass random or block copolymers

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WO 97/04068 PCT/US96/10843
12
where one monomer type is an amine N-oxide and the other
monomer type is either an amine N-oxide or not. The amine
oxide unit of the polyamine N-oxides has a PKa < 10,
preferably PKa < 7, more preferred PKa < 6.
The polyamine N-oxide containing polymer can be obtained
in almost any degree of polymerisation. The degree of
polymerisation is not critical provided the material has
the desired water-solubility and dye-suspending power.
Typically, the average molecular weight of the polyamine
N-oxide containing polymer is within the range of about 500
to about 1000,000; preferably from about 1,000 to about
50,000, more preferably from about 2,000 to about 30,000,
most preferably from about 3,000 to about 20,000.
Such polymers having a net cationic charge include
polyvinylpyrrolidone (PVP) as well as copolymers of N-
vinylimidazole N-vinyl pyrrolidone, having an average
molecular weight range in the range about 5,000 to about
100,000,preferably about 5,000 to about 50,000; said
copolymers havlng a molar ratio of N-vinylimidazole to N-
vinylpyrrolidone from about 1 to about 0.2, preferably from
about 0.8 to about 0.3.
Other optional ingredients include :
Additional softening agents : which are nonionic fabric
softener materials. Typically, such nonionic fabric
softener materials have a HLB of from about 2 to about 9,
more typically from about 3 to about 7. Such nonionic
fabric softener materials tend to be readily dispersed
either by themselves, or when combined with other materials
such as single-long-chain alkyl cationic surfactant
described in detail hereinafter. Dispersibility can be
improved by using more single-long-chain alkyl cationic
surfactant, mixture with other materials as set forth
hereinafter, use of hotter water, and/or more agitation.
In general, the materials selected should be relatively
crystalline, higher melting, (e.g. >40~C) and relatively
water-insoluble.

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WO 97/04068 PCT/US96/10843
13
The level of optional nonionic softener in the
compositions herein is typically from about 0.1% to about
10%, preferably from about 1% to about 5%.
Preferred nonionic softeners are fatty acid partial
esters of polyhydric alcohols, or anhydrides thereof,
wherein the alcohol, or anhydride, contains from 2 to 1~,
preferably from 2 to 8, carbon atoms, and each fatty acid
moiety contains from 12 to 30, preferably from 16 to 20,-
carbon atoms. Typically, such softeners contain from one
to 3, preferably 2 fatty acid groups per molecule.
The polyhydric alcohol portion of the ester can be
ethylene glycol, glycerol, poly (e.g., di-, tri-, tetra,
penta-, and/or hexa-) glycerol, xylitol, sucrose,
erythritol, pentaerythritol, sorbitol or sorbitan.
Sorbitan esters and polyglycerol monostearate are
particularly preferred.
The fatty acid portion of the ester is normally derived
from fatty acids having from 12 to 30, preferably from 16
to 20, carbon atoms, typical examples of said fatty acids
being lauric acid, myristic acid, palmitic acid, stearic
acid and behenic acid.
Highly preferred optional nonionic softening agents for
use in the present invention are the sorbitan esters, which
are esterified dehydration products of sorbltol, and the
glycerol esters.
Commercial sorbitan monostearate is a suitable material.
Mixtures of sorbitan stearate and sorbitan palmitate having
stearate/palmitate weigt ratios varying between about 10:1
and about 1:10, and 1,5-sorbitan esters are also useful.
Glycerol and polyglycerol esters, especially glycerol~
diglycerol, triglycerol, and polyglycerol mono- and/or di
esters, preferably mono-, are preferred herein (e.gO
polyglycerol monostearate with a trade name of Radiasurf
7248).
Useful glycerol and polyglycerol esters include mono-
esters with stearic, oleic, palmitic, lauric, isostearic,
myristic, and/or behenic acids and the diesters of stearic,

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W097/04068 PCT~S96/10843
14
oleic, palmitic, lauric, isostearic, behenic, and/or
myristic acids. It is understood that the typical mono-
ester contains some di- and tri-ester, etc.
The "glycerol esters" also include the polyglycerol,
e.g., diglycerol through octaglycerol esters. The
polyglycerol polyols are formed by condensing glycerin or
epichlorohydrin together to link the glycerol moieties via
ether linkages. The mono- and/or diesters of the
polyglycerol polyols are preferred, the fatty acyl groups
typically being those described hereinbefore for the
sorbitan and glycerol esters.
Surfactant/Concentration Aids
Although as stated before, relatively concentrated
compositions of the unsaturated material of Formula (I)
and (II) above can be prepared that are stable without the
addition of concentration aids, the concentrated
compositions of the present invention may require organic
and/or inorganic concentration aids to go to even higher
concentrations and/or to meet higher stability standards
depending on the other ingredients.
Surfactant concentration aids are typically selected from
the group consisting of single long chain alkyl cationic
surfactants; nonionic surfactants; amine oxides; fatty
acids; or mixtures thereof, typically used at a level of
from 0 to about l5~ of the composition.
Such mono-long-chain-alkyl cationic surfactants useful in
the present invention are, preferably, quaternary ammonium
salts of the general formula :
[ R2N+R3 ] X-
wherein the R2 group is Clo-C22 hydrocarbon group,
preferably Cl2-Clg alkyl group of the corresponding ester
linkage interrupted group with a short alkylene ~Cl-C4)
group between the ester linkage and the N, and having a
similar hydrocarbon group, e.g., a fatty acid ester of
choline, preferably Cl2-Cl4 (coco) choline ester and/or

CA 02227341 1998-01-19
W O 97/04068 PCT~US96/10843 1 5
C16-C1g tallow choline ester at from about 0.1~ to about
20% by weight of the softener active. Each R is a Cl-C4
alkyl or substituted ~e.g., hydroxy) alkyl, or hydrogell,
preferably methyl, and the counterion X~ is a softener
compatible anion, for example, chloride, bromide, methyl
sulfate, etc.
Other cationic materials with ring structures such as
alkyl imidazoline, imidazolinium, pyridine, and pyridinium
salts having a single C12-C30 alkyl chain can also be used.
Very low pH is required to stabilize, e.g., imidazoline
ring structures.
Some alkyl imidazolinium salts and their imidazoline
precursors useful in the present invention have the general
formula :
CH2--CH2
f ' ~R6 x
wherein y2 is -C(O)-O-, -O-(O)C-, -C(o)-N(R5)-, or
-N(R5)-C(o)- in which R5 is hydrogen or a Cl-C4 alkyl
radical; R6 is a Cl-C4 alkyl radical or H (for imidazoline
precursors); R7 and R8 are each independently selected from
R and R2 as defined hereinbefore for the single-long-chain
cationic surfactant with only one being R2.
Some alkyl pyridinium salts useful in the present
invention have the general formula :
2 + ~
R N ~ X
~ wherein R2 and X- are as defined above. A typical
material of this type is cetyl pyridinium chloride.
Nonionic Surfactant (Alkoxylated Materials)

CA 0222734l lsss-ol-ls
W097/04068 PCT~S96/10843
16
Suitable nonionic surfactants for use herein include
addition products of ethylene oxide and, optionally,
propylene oxide, with fatty alcohols, fatty acids, fatty
amines, etc.
Suitable compounds are substantially water-soluble
surfactants of the general formula :
R2 _ y _ (C2H40) z - C2H40H
wherein R2 is selected from the group consisting of
primary, secondary and branched chain alkyl and/or acyl
hydrocarbyl groups; primary, secondary and branched chain
alkenyl hydrocarbyl groups; and primary, secondary and
branched chain alkyl- and alkenyl-substituted phenolic
hydrocarbyl groups; said hydrocarbyl groups having a
hydrocarbyl chain length of from 8 to 20, preferably from
10 to 18 carbon atoms.
Y is typically -O-, -C(O)O-, -C(O)N(R)-, or
C(O)N(R)R-, in which R2 and R, when present, have the
meanings given hereinbefore, and/or R can be hydrogen, and
z is at least 8, preferably at least 10-11.
The nonionic surfactants herein are characterized by an
HLB (hydrophilic-lipophilic balance) of from 7 to 20,
preferably from 8 to 15.
Examples of particularly suitable nonionic surfactants
include
Straight-Chain, Primary Alcohol Alkoxylates such as
tallow alcohol-EO(11), tallow alcohol-EO(18), and tallow
alcohol-EO(25);
Straight-Chain, Secondary Alcohol Alkoxylates such as 2-
C16E~(ll); 2-C2oEO(11); and 2-C16EO(14);
Alkyl Phenol Alkoxylates, such as p-tridecylphenol EO(ll)
and p-pentadecylphenol EO(18), as well as
Olefinic Alkoxylates, and Branched Chain Alkoxylates such
as branched chain primary and secondary alcohols which are
available from the well-known "OXO" process.

CA 02227341 1998-01-19
WO 97/04068 PCT/US96/10843
17
Amine Oxides
.
Suitable amine oxides include those with one alkyl or
hydroxyalkyl moiety of 8 to 28 carbon atoms, preferably
from 8 to 16 carbon atoms, and two alkyl moieties selected
from the group consisting of alkyl groups and hydroxyalkyl
groups with 1 to 3 carbon atoms.
Exa~nples include dimethyloctylamine oxide,
diethyldecylamine oxide, bis-(2-hydroxyethyl)dodecylamine
oxide, dimethyldodecyl-amine oxide, dipropyltetradecyl~nine
oxide, methylethylhexadecylamine oxide, dimethyl-2-
hydroxyoctadecylamine oxide, and coconut fatty alkyl
dimethylamine oxide.
Fatty Acids
Suitable fatty acids include those containing from 12 to
25, preferably from 16 to 20 total carbon atoms, with the
fatty moiety containing from 10 to 22, preferably from 10
to 14 (mid cut), carbon atoms. The shorter moiety contains
from l to 4, preferably from 1 to 2 carbon atoms.
Electrolyte Concentration Aids
Inorganic viscosity control agents which can also act
like or augment the effect of the surfactant concentration
aids, include water-soluble, ionizable salts which can also
optionally be incorporated into the compositions of the
present invention. A wide variety of ionizable salts can
be used. Exarnples of suitable salts are the halides of the
Group IA and IIA metals of the Periodic Table of the
Elements, e.g., calcium chloride, magnesium chloride,
sodium chloride, potassium bromide, and lithium chloride.
The ionizable salts are particularly useful during the
process of m; xi ~g the ingredients to make the compositions
herein, and later to obtiain the desired visCosity~ The

CA 02227341 1998-01-19
W097/04068 PCT~S96/10843
18
amount of ionizable salts used depends on the amount of
active ingredients used in the compositions and can be
adjusted according to the desires of the formulator.
Typical levels of salts used to control the composition
viscosity are from about 20 to about 20,000 parts per
million (ppm), preferably from about 20 to about ll,000
ppm, by weight of the composition.
Alkylene polyammonium salts can be incorporated into the
composition to give viscosity control in addition to or in
place of the water-soluble, ionizable salts above. In
addition, these agents can act as scavengers, forming ion
pairs with anionic detergent carried over from the main
wash, in the rinse, and on the fabrics, and may improve
softness performance. These agents may stabilize the
viscosity over a broader range of temperature, especially
at low temperatures, compared to the inorganic
electrolytes.
Specific examples of alkylene polyammonium salts include
l-lysine monohydrochloride and l,5-diammonium 2-methyl
pentane dihydrochloride.
Another optional ingredient is a liquid carrier. The
liquid carrier employed in the instant compositions is
preferably at least primarily water due to its low cost
relative availability, safety, and environmental
compatibility. The level of water in the liquid carrier is
preferably at least about 50%, most preferably at least
about 60%, by weight of the carrier. Mixtures of water and
low molecular weight, e.g., <about 200, organic solvent,
e.g., lower alcohol such as ethanol, propanol, isopropanol
or butanol are useful as the carrier liquid. Low molecular
weight alcohols include monohydric, dihydric (glycol, etc.)
trihydric ~glycerol, etc.), and higher polyhydric (polyols)
alcohols.
Still other optional ingredients are stabilizers, such as
well known antioxidants and reductive agents, Soil Release
Polymers, thickeners, emulsifiers, bacteriocides,
colorants, perfumes, preservatives, optical brighteners,

CA 02227341 1998-01-19 ,.
wos7/o4o68 PCT~S96/10843
19
anti ionisation agents, antifoam agents, enzymes and the
like.
~ The invention will be further illustrated by means of
the following examples.

CA 0222734l lsss-ol-ls
W097/04068 PCT~S96/10843
EXAMPLES
Example I
The following liquid fabric softening compositions
with the respective VitasynR dyes were prepared and tested
for stain removal and hueing.
1 2 3
DEEDMAC 20 18 18
Fatty acid - 2 2
Hydrochloric acid 0.02 0.02 0.02
Silicone emulsion 0.01 0.01 0.01
Soil release polymer 0.2 0.2 0.2
Polyethyleneglycol 0.6 0.6 0.6
Calcium chloride 0.013 0.013 0.013
Vitasyn Blue V85 0.0012 0.0012 0.0008
Vitasyn Red 4RC 0.0003 0.0003
Vitasyn Yellow XX90 - - 0.0012
Perfume 1.0 1.0 1.0
Balance Up to 100%
Example II
Staining test
Stains with fabric softening product were made on dry
and wet fabrics as well. The fabric softening product
contains either commercial available current used dyes or
VitasynR dyes according to the invention.
Of the fabrics replicas were made and delivered into four
legs viz.
a. untreated;
b. cold rinse (in water only);
c. washed with detergent composition at 40~C;
d. washed with detergent composition at 60~C.

CA 02227341 lgss-ol-ls
Wos7/04068 PCT~S96/10843
21
The results are shown in the following table :
S~ ni r~g gradQs after different ~ 1 treatments
R~ference Vitasyn
~ blue dyQ Blue
Wet fabric As is 4.5 4.5
(muslin After a rinse in cold 3 3.5
cotton) water
after a 40~C wash 3.5 0
after a 60~wash 1 0
Dry fabric As is 5 5
(muslin After a rinse in cold 2 2
cotton) water
after a 40~C wash 3.5 0
after a 60~C wash 2 0
Wet fabric As is 5 5
(polycotton) After a rinse in cold 0.5
water
after a 40~C wash 1.5 0
after a 60~C wash 0 0
Dry fabric As is 5 5
(polycotton) After a rinse in cold 1 1.5
water
after a 40~C wash 2 0
after a 60~C wash 0 0
(0 = No stain, 5 = very intense stain)
Vitasyn blue dye delivers a significant improvement in
terms of staining. Stains with Vitasyn Blue are fully
removed at 40~C or at 60~C wash, as opposed to the current
(reference) blue dye.

CA 0222734l lsgs-ol-lg
W097/04068 PCT~S96/10843
22
Example III
Hueing test
White swatches were cumulative washed (1-20 cycles)
with detergent composition and fabric softener composition
accordingly with eiter reference Blue dye or Vitasyn Blue
dye.
The results obtained are shown in the following table :
Ul~i ng qrading (PSU) vs. current blue dye
Reference Blue Vitasyn Blue
1 cycle -1.3 -0.3
5 cycles -0.8 +0.5
10 cycles ~1.3 +1.8
15cycles -0.4 +0.2
20 cycles +l.ls +1.4s
Average grad~ -0.1 +0.8
The above shows that Vitasyn blue dye has a
directionally better hueing profile than current reference
blue dye (the higher the number, the less hueing).

Representative Drawing

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Administrative Status

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Event History

Description Date
Inactive: IPC from MCD 2006-03-12
Application Not Reinstated by Deadline 2002-06-25
Time Limit for Reversal Expired 2002-06-25
Inactive: Abandoned - No reply to s.30(2) Rules requisition 2001-10-03
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2001-06-26
Inactive: S.30(2) Rules - Examiner requisition 2001-04-03
Inactive: IPC assigned 1998-04-30
Inactive: IPC assigned 1998-04-30
Inactive: First IPC assigned 1998-04-30
Classification Modified 1998-04-30
Inactive: Acknowledgment of national entry - RFE 1998-04-16
Application Received - PCT 1998-04-14
Request for Examination Requirements Determined Compliant 1998-01-19
Amendment Received - Voluntary Amendment 1998-01-19
All Requirements for Examination Determined Compliant 1998-01-19
Application Published (Open to Public Inspection) 1997-02-06

Abandonment History

Abandonment Date Reason Reinstatement Date
2001-06-26

Maintenance Fee

The last payment was received on 2000-03-23

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

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

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

Fee History

Fee Type Anniversary Year Due Date Paid Date
Registration of a document 1998-01-19
Basic national fee - standard 1998-01-19
Request for examination - standard 1998-01-19
MF (application, 2nd anniv.) - standard 02 1998-06-25 1998-01-19
MF (application, 3rd anniv.) - standard 03 1999-06-25 1999-03-26
MF (application, 4th anniv.) - standard 04 2000-06-26 2000-03-23
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE PROCTER & GAMBLE COMPANY
Past Owners on Record
DIDIER PEROT
DOMINIQUE LECLUYSE
JACQUY DE PAUW
KAREL ENGELS
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 1998-01-18 22 810
Abstract 1998-01-18 1 44
Claims 1998-01-18 3 77
Claims 1998-01-19 3 75
Notice of National Entry 1998-04-15 1 202
Courtesy - Certificate of registration (related document(s)) 1998-04-15 1 117
Courtesy - Certificate of registration (related document(s)) 1998-04-15 1 117
Courtesy - Abandonment Letter (Maintenance Fee) 2001-07-23 1 182
Courtesy - Abandonment Letter (R30(2)) 2001-12-11 1 171
PCT 1998-01-18 10 333